Inadequately posted:

I was going to get into this discussion later, but since it's been brought up, for the most part my disillusionment with the game stems from how it ends up, rather than how it starts out. I certainly don't think the game's entirely irredeemable - if it was, I wouldn't be showing it off. It's largely a matter of unfulfilled potential.

The main issue with the first case is that it hinges around an impossible promise they'd never be able to fully commit to ("let's throw the player into the sleaziest, most twisted and hosed-up place on the Net"), but in broad strokes the central premise of "kid who thinks he's hot poo poo gets swept up into something way over his head" is still a decent core for the first case. There's also the issue, as people have pointed out, that both sides involved in the central conflict are such terrible people that by the end of it you mostly just want to wash your hands of the whole affair - not necessarily a bad thing if that's the tone you're going for, but it certainly doesn't endear the game to most people. A minor change I'd probably make on that front would be to have Timmy as the one who contacted you in a panic, with Geoffrey Haggis as the disapproving figure who insists on being the Big Man that wants to settle this affair all by himself. That way, when Fredo is rescued we get a reminder that there are people who (even if it's for somewhat misguided reasons) actually care for Fredo for who he is, rather than "hooray, we returned Fredo to...his clearly abusive father "

We haven't finished the second case yet, but for the most part I think it's pretty solid. Might have one too many cheap shots at Farmville and other mobile games of that ilk for my liking, but by and large this case could probably be run largely unchanged in any successful incarnation of this game.

The third case, however, is where the metaplot starts to factor more and more heavily into the game's storyline, largely to its detriment. We'll get more into why that is later, but for the most part the ways in which the game goes downhill are fairly self-evident.