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ChineseBuffet
Mar 7, 2003

Subvisual Haze posted:

Do I understand correctly that long-term capital losses are actually worse than short-term capital losses? Because they will subtract from your long-term capital gains first, which would otherwise be taxed preferentially?

Yes.

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Subvisual Haze
Nov 22, 2003

The building was on fire and it wasn't my fault.

Thank you. That is very stupid, but I doubt I'm the first person to have that thought.

Flash Gordon
May 8, 2006
Death To Ming
I need to file an extension and pay my estimated taxes for the first time because I'm only just receiving some of the documents I need and the accountant I've previously worked with won't be able to get around to me in time.

What's the best way to start doing this? I paid estimated quarterly taxes for Q4 2022 in January with the help of this accountant - my tax situation was very different last year due for a variety of reasons and I do not feel confident I could have done this myself. I feel like I'm in a bit of a catch-22 where I am not going to be able to get an accountant to help in time but I might need one to help figure out how much I owe.

Busy Bee
Jul 13, 2004
Edit

Busy Bee fucked around with this message at 07:41 on Mar 29, 2023

H110Hawk
Dec 28, 2006

Flash Gordon posted:

I need to file an extension and pay my estimated taxes for the first time because I'm only just receiving some of the documents I need and the accountant I've previously worked with won't be able to get around to me in time.

What's the best way to start doing this? I paid estimated quarterly taxes for Q4 2022 in January with the help of this accountant - my tax situation was very different last year due for a variety of reasons and I do not feel confident I could have done this myself. I feel like I'm in a bit of a catch-22 where I am not going to be able to get an accountant to help in time but I might need one to help figure out how much I owe.

It depends on how much you're worried about overpayment vs underpayment + penalties. All they ask is that you have paid at least the amount actually due on your return. You can always overshoot and call it a day. Depending on how complicated you can just take your W-2 income, subtract the standard deduction, subtract any trad 401k you did, add in the 1099-B/1099-INT amounts, look up the result in the tax tables, then subtract the withholding from your W-2 and any estimated payments you've done. If the number is positive, pay that amount, fill out the extension and mail it in. If it's negative all you have to do is fill it out.

It only gets tricky when you want to be precise and actually account accurately for things like basis, double counted income (ESPP), ISO upside, business expenses, that sort of thing.

Ungratek
Aug 2, 2005


Subvisual Haze posted:

Thank you. That is very stupid, but I doubt I'm the first person to have that thought.

It makes complete sense and I’m not sure why you would think otherwise

Subvisual Haze
Nov 22, 2003

The building was on fire and it wasn't my fault.

Ungratek posted:

It makes complete sense and I’m not sure why you would think otherwise

If the goal is to encourage investors to hold investments longer-term (as seems to be the case with long term cap gains having a lower tax rate), then the current method seems to be working at cross purposes as it encourages you to sell losses earlier.

KillHour
Oct 28, 2007


I'm not an accountant, but if you could use long term losses to offset short term gains, I'm pretty sure someone would set up a pair of funds where you invest in both and one takes a dollar and turns it into a million $ in gains and the other turns a dollar into a million $ in losses. Then if you have 100k in short term gains, you cash in 10% of each and oh look now it's all long term gains how strange.

Ungratek
Aug 2, 2005


Subvisual Haze posted:

If the goal is to encourage investors to hold investments longer-term (as seems to be the case with long term cap gains having a lower tax rate), then the current method seems to be working at cross purposes as it encourages you to sell losses earlier.

Market historically goes up over long periods so you’re more likely to have gains than losses on your long term holdings. You also get to use your long term losses against short term gains, provided you’ve already wiped out the long term gains in that year (and vice versa with short term losses against long term gains).

You should always match losses and gains of the same type against each other before using them against other items. It’s a basic rule of tax and accounting, and the thing that makes tax frustrating is when it doesn’t adhere to these rules, which is not something 98% of taxpayers have to encounter.

Centzon Totochtin
Jan 2, 2009
I need to file an extension because there's an issue with my W-2 (I only worked in one state and county the entire year so local and state wages SHOULD be the same but aren't for some reason, difference is about $3.7k) and the payroll company that handles it says it won't be able to fix it before the normal filing deadline. I have an uncomplicated tax situation so I usually self-file. I'm just a bit confused how to file for the extension.

https://www.irs.gov/forms-pubs/extension-of-time-to-file-your-tax-return

My AGI is less than $73K so do I just use one of the Free File options and then amend it later when I get my corrected W-2? Do I need to submit form 4868? It needs me to declare my estimated tax liability but I won't know how much that is unless I actually file, right? I'm in NY if that matters at all, would I need to file for an extension separately with the state as well?

E: I typically use turbotax free, is there any reason to not use that again and use one of those linked on the IRS website instead?

Centzon Totochtin fucked around with this message at 20:11 on Mar 29, 2023

H110Hawk
Dec 28, 2006
Do you normally get a refund? Did anything change this year materially such as a new job, new spouse, lack of spouse, etc?

If so just put your current federal withholding amount from the w-2 in the slip and send it in. It truly does not matter if you're getting a refund.

Centzon Totochtin
Jan 2, 2009
No, I usually owe between $300-1000. Nothing changed that would affect my filing status

I was able file the federal extension via turbotax, the problem now is Im trying to file my NY state extension and don't know how to calculate how much I owe. It's asking if I need to make a payment with my extension but.... I don't know if I need to. Some years I get a small state refund, sometimes I owe a small amount (last year I owed $15).

H110Hawk
Dec 28, 2006
If you normally owe $300-1000 then I would just pay the grand and add it to your current withholding amount as the estimated due. For the state I would just assume it's zero and eat any interest in the next month or three.

Or just free file (never pay if you qualify, gently caress intuit) and amend it later when you get the w-2c.

BeanpolePeckerwood
May 4, 2004

I MAY LOOK LIKE SHIT BUT IM ALSO DUMB AS FUCK



intuit finally lost my business because their poo poo don't load. thank you goons. thank you freetaxusa (not a scam)

Centzon Totochtin
Jan 2, 2009

H110Hawk posted:

For the state I would just assume it's zero and eat any interest in the next month or three.


This is what I ended up doing, but will it affect my credit score at all?

sullat
Jan 9, 2012

Centzon Totochtin posted:

This is what I ended up doing, but will it affect my credit score at all?

No

neogeo0823
Jul 4, 2007

NO THAT'S NOT ME!!

Hey, thread. I have a question that is hopefully an easy one to answer.

My wife and I live in Western New York. Like, west of Rochester, so we're not in Yonkers or any other weird tax zones. She's self-employed, renting a space from a person who owns a building. What's the appropriate way file our taxes? She's convinced that we need to file Married Filing Separate, that she needs to file her business' taxes by herself, and I need to do mine by myself, and that's it. Is that the case? Does my wife need to file taxes for her business, and then somehow also for herself if she's the one that pays herself? Or do we file jointly, and she files her business taxes in with that? Or what? This is the first year we've been in this situation and we're confused as gently caress, and I just don't want to screw this up really bad or anything.

Missing Donut
Apr 24, 2003

Trying to lead a middle-aged life. Well, it's either that or drop dead.

neogeo0823 posted:

Hey, thread. I have a question that is hopefully an easy one to answer.

My wife and I live in Western New York. Like, west of Rochester, so we're not in Yonkers or any other weird tax zones. She's self-employed, renting a space from a person who owns a building. What's the appropriate way file our taxes? She's convinced that we need to file Married Filing Separate, that she needs to file her business' taxes by herself, and I need to do mine by myself, and that's it. Is that the case? Does my wife need to file taxes for her business, and then somehow also for herself if she's the one that pays herself? Or do we file jointly, and she files her business taxes in with that? Or what? This is the first year we've been in this situation and we're confused as gently caress, and I just don't want to screw this up really bad or anything.

Unless her business is a partnership or a corporation it does not have a separate federal income tax filing. Having a business would not generally the reason to switch to separate filing unless there are extenuating circumstances (such as a need to keep tax debts separate).

If your wife is wrong about these two issues, it’s a pretty solid sign to me that she should not be self-preparing the return. And if you’re not confident in filing a return with the business, it might be a year that you are best off seeing a professional.

H110Hawk
Dec 28, 2006
I would hire a pro at least for this year. If you wind up looking at the outcome and it's super easy don't do it next year. They can pretty easy handle knowing if you should MFJ vs MFS. Just like people hire your wife for her specialized knowledge, hire a tax person for theirs.

Centzon Totochtin
Jan 2, 2009
I got my corrected W-2 ahead of time. So when I file, I should just all the numbers and info from the W-2C and completely disregard the original W-2, right?

neogeo0823
Jul 4, 2007

NO THAT'S NOT ME!!

Missing Donut posted:

Unless her business is a partnership or a corporation it does not have a separate federal income tax filing. Having a business would not generally the reason to switch to separate filing unless there are extenuating circumstances (such as a need to keep tax debts separate).

If your wife is wrong about these two issues, it’s a pretty solid sign to me that she should not be self-preparing the return. And if you’re not confident in filing a return with the business, it might be a year that you are best off seeing a professional.

H110Hawk posted:

I would hire a pro at least for this year. If you wind up looking at the outcome and it's super easy don't do it next year. They can pretty easy handle knowing if you should MFJ vs MFS. Just like people hire your wife for her specialized knowledge, hire a tax person for theirs.

Thanks for this. I've convinced her to seek out a professional for official advice. She was convinced she needed to file separate because a person she knows who's in a similar situation does. I just keep thinking back to when we filed MFS back in 2018 for... reasons I honestly can not recall at the moment, and she got back like $180 or something, when we were expecting over $1000 back. It was a bad year, that I'm not wanting to experience again. Obviously, whatever the professional recommends is what we'll go with, it's just that I'd really like to hear proper reasoning for whatever we do beyond "this person I know does it this way, so I should do it this way".

Are there recommended tax prep services I should look for? I'm inclined to want to shop local, if possible, but if you guys end up swearing by some specific service or another, then obviously I'll weigh that in as well.

neogeo0823 fucked around with this message at 00:27 on Apr 1, 2023

H110Hawk
Dec 28, 2006
I swear by shopping local. Ask around and talk to people who use folks to prep their taxes. Ask them what's complicated about their taxes. Plenty of people have completely uncomplicated taxes who really want to talk to someone in person "to get the biggest return" when in reality they just need to use a online service. Once there, email and ask to be put on the list for after April 15th and go talk to these people.

In the mean time file extensions for everything. Just do an MFJ extension for you guys because it doesn't matter at all and you can change it later.

In the mean time I would insist on making people tell you the "why" because people get it wrong constantly. It's like worrying about the gift tax or trying to itemize when they have like $10k in deductions MFJ.

Salt Fish
Sep 11, 2003

Cybernetic Crumb
Can one of you lawyers please give me some official legal advice and represent me for this question:

I work from home. Is it a tax issue if I move to Washington state and don't tell my employer? If I maintain a PO box in VA, continue paying taxes there, and just never update my employer is that some kind of tax fraud? The key thing here is that Washington doesn't have an income tax.

How many days can you work in another state like that before its an issue? It must be different for each state?

mrmcd
Feb 22, 2003

Pictured: The only good cop (a fictional one).

Not a lawyer, but living in one state full-time while representing to your employer that you live in a completely different one certainly sounds fraud-ish. But also.. why would you lie about living in a state with an income tax while actually living in a state without one?

Salt Fish
Sep 11, 2003

Cybernetic Crumb
Its a long story but basically I'm remote but not allowed to move out of the state, but gently caress those busy bodies, what if I want to spend the summer somewhere else, for example at a friend's house or with family?

H110Hawk
Dec 28, 2006

Salt Fish posted:

Its a long story but basically I'm remote but not allowed to move out of the state, but gently caress those busy bodies, what if I want to spend the summer somewhere else, for example at a friend's house or with family?

You are setting up your employer for various legal liability things relating to unemployment, workers comp, paid family leave, and payroll tax reporting. They will likely fire you on the spot when they figure it out.

Salt Fish
Sep 11, 2003

Cybernetic Crumb

H110Hawk posted:

You are setting up your employer for various legal liability things relating to unemployment, workers comp, paid family leave, and payroll tax reporting. They will likely fire you on the spot when they figure it out.

Okay with all due respect you're clearly wrong if you think about it for more than a few seconds. For example, if I log in and send an email from an airport layover, that isn't a taxable event. As far as I can tell it varies between 18 and 182 days depending on the state.

edit:
"Resident -- A person who lives in Virginia, or maintains a place of abode here, for more than 183 days during the year, or who is a legal (domiciliary) resident of the Commonwealth, is considered a Virginia resident for income tax purposes. Residents file Form 760."

https://www.tax.virginia.gov/residency-status#:~:text=Resident%20%2D%2D%20A%20person%20who,Residents%20file%20Form%20760.

So if I live in VA for 183+ days per year there's no change in status in VA, and in WA:

"The Department of Revenue presumes that a person is a resident of this state if he or she does any of the following:

- Maintains a residence in Washington for personal use;
- Lives in a motor home or vessel which is not permanently attached to any property if the person previously lived in this state and does not have a permanent residence in any other state;
- Is registered to vote in this state;
- Receives benefits under one of Washington's public assistance programs;
- Has a state professional or business license in this state;
- Is attending school in this state and paying tuition as a Washington resident or is a custodial parent with a child attending a public school in this state;
- Uses a Washington address for federal or state taxes;
- Has a Washington State driver's license; or
- Claims Washington as a residence for obtaining a hunting or fishing license, eligibility to hold public office or for judicial actions."

So if I rented a place there for 30 days, that could only fall under "- Maintains a residence in Washington for personal use" and I doubt that applies.
https://dor.wa.gov/contact/washington-state-residency-definition

Salt Fish fucked around with this message at 02:24 on Apr 3, 2023

Epi Lepi
Oct 29, 2009

You can hear the voice
Telling you to Love
It's the voice of MK Ultra
And you're doing what it wants
If you only want to listen to the answer that you already wanted to hear why did you bother asking for help?

gently caress off it's tax season and we don't have time for stupidity. Just go gently caress around and hope you don't find out.

skipdogg
Nov 29, 2004
Resident SRT-4 Expert

H110Hawk posted:

You are setting up your employer for various legal liability things relating to unemployment, workers comp, paid family leave, and payroll tax reporting. They will likely fire you on the spot when they figure it out.

Yep. My large Fortune 100 company makes it clear to us this is a huge deal. No working from other states and especially outside of the country. It’s a big rear end liability and the size of the company makes us a huge target for states to come after us.

Folks who do travel for work coordinate with HR/Payroll to make sure we’re compliant with local laws.

H110Hawk
Dec 28, 2006

Salt Fish posted:

Okay with all due respect you're clearly wrong if you think about it for more than a few seconds. For example, if I log in and send an email from an airport layover, that isn't a taxable event. As far as I can tell it varies between 18 and 182 days depending on the state.

lol ok have fun, you said "move to washington." They can also just fire you because they want to, or because you're a prick, and no amount of "but ackshually" is going to change that.

Missing Donut
Apr 24, 2003

Trying to lead a middle-aged life. Well, it's either that or drop dead.

Salt Fish posted:

As far as I can tell it varies between 18 and 182 days depending on the state.

It’s incredible that you can be so arrogant when you have so little clue about what you’re talking about. That is absolutely not the rule.

A couple years ago, one of my clients had a Virginia filing requirement because he worked two days in the state. This year alone, I’ve done state returns with about a week’s worth of wages in CO, NC, and NY.

But if you’re so sure that you know more about multistate taxation than the tax professionals you were asking advice from and the payroll departments of our clients, just do whatever you want. Just don’t ask us for help on how much tax to have withheld from your unemployment insurance benefit.

Salt Fish
Sep 11, 2003

Cybernetic Crumb

Missing Donut posted:

It’s incredible that you can be so arrogant when you have so little clue about what you’re talking about. That is absolutely not the rule.

Its really not that incredible.

Missing Donut posted:

This year alone, I’ve done state returns with about a week’s worth of wages in CO, NC, and NY.

Yeah this is what I expect, there should be some specific amount of dollars or specific amount of days that triggers a requirement; like it has a specific quality that can be described in text right.

Epi Lepi
Oct 29, 2009

You can hear the voice
Telling you to Love
It's the voice of MK Ultra
And you're doing what it wants
Speaking of multi-state filing requirements, I have an issue I'm not sure how to handle for a new client. He is a musician who operates as an S Corporation. His S Corp is NY based and also registered in CA and MA for sure and I think like CT or something. Last year he did some shows in NJ and TN. If he was operating as a single member LLC or just as himself I would file a non-resident NJ return for the income from that show and that would be that since TN doesn't have an income tax anymore.

I'm not sure if his S Corporation has a filing requirement in those states and his entertainment lawyer did not have him register the corporation in those states (which is very annoying as I can't even e-file extensions electronically without having file numbers from those states so I can't punt the question to after April 18th).

If someone has first hand experience with this sort of thing I would appreciate some help, if not I would take some direction on what sources I can use to figure out if he truly needs to file something for those states at the entity level.

Missing Donut
Apr 24, 2003

Trying to lead a middle-aged life. Well, it's either that or drop dead.

Epi Lepi posted:

\If someone has first hand experience with this sort of thing I would appreciate some help, if not I would take some direction on what sources I can use to figure out if he truly needs to file something for those states at the entity level.

A lot of states issue specific guidance on the taxation of nonresident entertainers and there are usually specific tax code citations. Maybe Tennessee doesn’t (due to no personal income tax) but I’m pretty sure I have something on New Jersey somewhere.

An S corp musician sounds like a special layer of hell to deal with, though. I hope the client at least makes enough to justify the entity.

Peyote Panda
Mar 10, 2019

Missing Donut posted:

Just don’t ask us for help on how much tax to have withheld from your unemployment insurance benefit.
TBF if they're fired for misconduct at their workplace then unemployment insurance income may not be an issue.

Salt Fish posted:

Yeah this is what I expect, there should be some specific amount of dollars or specific amount of days that triggers a requirement; like it has a specific quality that can be described in text right.
First, what people in this thread keep trying to explain is that it's not that simple -- the triggers will vary greatly not just from one state to the next but also with the category of employment, the type of work being done, the length of time, etc. Which is why you'd normally contact your HR/payroll department to sort it out based on all of those multivariate factors. (Edit: And also why a lot of employers try to avoid the headache of doing so if possible, which is probably part of the reason for your current employer's policy, tied in with the liability issues noted earlier in the thread.)

Unfortunately this runs into the second issue, which is that you can't do that because it involves your plan to violate a condition of your employment without telling your employer, which could easily lead to you being fired if they find out. And if that happens not only are you out of a job but then you get the fun of trying to find a preparer you'll have to pay extra to sort out your multi-state tax mess as well.

Peyote Panda fucked around with this message at 09:15 on Apr 3, 2023

mrmcd
Feb 22, 2003

Pictured: The only good cop (a fictional one).

Peyote Panda posted:

Unfortunately this runs into the second issue, which is that you can't do that because it involves your plan to violate a condition of your employment without telling your employer, which could easily lead to you being fired if they find out. And if that happens not only are you out of a job but then you get the fun of trying to find a preparer you'll have to pay extra to sort out your multi-state tax mess as well.

Yeah this is the main problem. Nobody is gonna care if you take a vacation and hang out with your buddy in another state for a few weeks and reply to some emails while you're there. But sending all your mail to a PO box and (presumably) not having a residence in VA and instead living, like, wherever man, means you're not a resident of VA. Taxes aren't the issue here.

KYOON GRIFFEY JR
Apr 12, 2010



Runner-up, TRP Sack Race 2021/22

Salt Fish posted:

Okay with all due respect you're clearly wrong if you think about it for more than a few seconds. For example, if I log in and send an email from an airport layover, that isn't a taxable event. As far as I can tell it varies between 18 and 182 days depending on the state.

edit:
"Resident -- A person who lives in Virginia, or maintains a place of abode here, for more than 183 days during the year, or who is a legal (domiciliary) resident of the Commonwealth, is considered a Virginia resident for income tax purposes. Residents file Form 760."

https://www.tax.virginia.gov/residency-status#:~:text=Resident%20%2D%2D%20A%20person%20who,Residents%20file%20Form%20760.

So if I live in VA for 183+ days per year there's no change in status in VA, and in WA:

"The Department of Revenue presumes that a person is a resident of this state if he or she does any of the following:

- Maintains a residence in Washington for personal use;
- Lives in a motor home or vessel which is not permanently attached to any property if the person previously lived in this state and does not have a permanent residence in any other state;
- Is registered to vote in this state;
- Receives benefits under one of Washington's public assistance programs;
- Has a state professional or business license in this state;
- Is attending school in this state and paying tuition as a Washington resident or is a custodial parent with a child attending a public school in this state;
- Uses a Washington address for federal or state taxes;
- Has a Washington State driver's license; or
- Claims Washington as a residence for obtaining a hunting or fishing license, eligibility to hold public office or for judicial actions."

So if I rented a place there for 30 days, that could only fall under "- Maintains a residence in Washington for personal use" and I doubt that applies.
https://dor.wa.gov/contact/washington-state-residency-definition

Are you intending to spend 183+ days in Virgina to qualify as a resident? What you posted seems irrelevant considering you started off with "I'm moving to Washington" - are you intending to move there without doing any of the things in the list?

Small White Dragon
Nov 23, 2007

No relation.
The problem here is that if you live in that other state, you can potentially create a Nexus for your employer, meaning the State could hold them liable for corporate income taxes and so forth.

This is one of those things I wish Congress would finally sort out.

Centzon Totochtin
Jan 2, 2009
I'm filing my taxes now with my 44444/W-2C. I paid $507 in estimated federal taxes when I applied for the filing extension last week, which was accepted and already withdrawn from my checking account. Do I then declare that $507 as estimated federal taxes paid under additional payments (since it wasn't part of a quarterly federal tax payment)? Or will the IRS somehow figure it out themselves and refund me the difference if there is one/deduct it from what I owe (somehow doubting its this)

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H110Hawk
Dec 28, 2006

Centzon Totochtin posted:

I'm filing my taxes now with my 44444/W-2C. I paid $507 in estimated federal taxes when I applied for the filing extension last week, which was accepted and already withdrawn from my checking account. Do I then declare that $507 as estimated federal taxes paid under additional payments (since it wasn't part of a quarterly federal tax payment)? Or will the IRS somehow figure it out themselves and refund me the difference if there is one/deduct it from what I owe (somehow doubting its this)

You need to put the $507 in your 1040 as a payment.

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