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Quinctia
Jul 17, 2006

Disasterrific.
I haven't noticed a problem like that yet, however I'm not using my Touch to store a lot of music at the moment, I've been using it for apps and streaming radio, mostly.

I've got a couple gigs of music, and I didn't have a problem transferring. Aside from the quirks where iTunes doesn't always like to transfer album art to (any) iPod.

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Quinctia
Jul 17, 2006

Disasterrific.
They make 12V -> USB adapters for the car, and then you should be able to just use a lightning-ended cable with that. I don't know if that's a cheaper option overall or not?

Quinctia
Jul 17, 2006

Disasterrific.
The touch is like an iphone without the phone or a very small tablet, so if you're looking for something just for audio, you might think about picking up a nano. Especially if price is an important factor. I've been fond of the nano as an mp3 player. There are quite a few of the 8gb 6th gen nanos floating around, because folks were able to return 1st gen nanos under a recall, and that's what got sent back to them. So you could pick up a used 6th gen nano pretty cheaply.

If you're going to have access to free wifi, though, and want something that can browse the web, play some games, do streaming, the touch is pretty great. I use mine quite a bit. Also, the latest touch has a decent camera built in. I think it's worth the money if you're going into it thinking you've got a tiny, tiny tablet.

So for your questions:
- Yes, if you're going to use all its features, no if you just want an upgraded audio player.
- You should be fine, aside from incompatible file formats needing to be converted. Especially if you've already got things tagged and organized, unless your music is ALL WMV or something weird, it should be pretty painless.
- Well, the OS updates occasionally. I think there have been three updates pushed since I got mine in November. I've been holding off on the last one because I've been toying around with the idea of jailbreaking it. I think the only thing that postponing an OS update could interfere with would be compatibility with future app updates, as well as not gaining any of the benefits that an OS update fixed.
- Depends on how you'll be charging things? My touch only came with a USB->Lightning cable. So, if you're plugging the thing into a USB port in Europe, that won't be an issue. If you were planning on buying a proprietary Apple USB->Wall plugin thingie, then you'll need something to convert to the right wall jack for Europe. However, I have a cheapish surge protector with built in USB jacks that I use at home for charging, so you could probably pick up a similar product for use where you're going.

Quinctia
Jul 17, 2006

Disasterrific.
I think you'll be happy, then. I grabbed my cheap 6th gen just to listen to podcasts in bed, and its little clippy bit is great for not losing the drat thing.

Of course, the podcast app on my Touch has a sleep timer, so I'm not using the nano so often anymore.

Quinctia
Jul 17, 2006

Disasterrific.
I'd try replacing the cable. I can't say I've had that problem with mine, same capacity 5gen bought right after they launched. Although I've plugged various headphones into it, they've only been headphones. But that's multiple connectors plugged into the jack over time.

Also, between the car and whereever else you use it, is there a chance that the jack itself could be getting really dirty and/or plugged?

Where is the iPod in the car when it's plugged in? Is there a chance that it could be dangling from the cable and causing unusual stress to the jack?

I use an iPod in my car, but it's a Nano hooked up via a USB cable. My headunit had a rear USB input, so I've got the cable fished into the glove compartment...which keeps the iPod itself relatively secure while I'm driving.

Quinctia
Jul 17, 2006

Disasterrific.
Gamestop, Disc Replay, I know have them. Also, since a bunch of people with 1st Gen Nanos got 6th Gen ones in a recall, it might be easier to find a nice, barely used 6th Gen on the cheap.

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Quinctia
Jul 17, 2006

Disasterrific.
I'm suddenly glad my only issues with syncing are missing album art and my podcasts deleting themselves.

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