I loved GTA 3, but didn't play Vice city or San Andreas (got into MMOs that time, and thus, missed on many gems. I regret that... I realize MMO aren't really worth it). Anyway, I played Chinatown on my DSi, and GTA IV and V on my xbox 360. Loved them all.
Last year, I decided to give Vice City a try (so that's before GTA V), and I can say with confidence, that the game doesn't hold up. Driving mechanics are horrible, controls are unresponsive (I can't believe how much I fought with the controls... Makes me glad that things are much better in the current GTA), combat is lame, there are no checkpoints in missions, so if you have a long drive, cut-scene, action and then you die, you have to do everything again, which is incredible bore-some.
The story is predictable, the characters are lame, and the games makes you grind (by buying businesses or the like) and that's obligatory for the endgame. That's a chore.
The good side, is that missions are sometimes crazy and when you're not fighting the control and bad physics, the game can actually be fun.
But my bottom line is, that the game doesn't hold up well for today's standards. And I don't have the "nostalgia" factor that may bias my opinion. So it's something to consider.
Just because of that I don't wanna try San Andreas, I know it's a really long game, and my backlog is big enough. Maybe if I get some time, I might try it. I hope I don't end up disappointed again.