I work in Little Italy, and there are some things you should definitely consider.
1) How close to the train tracks will you be. This might not seem that big a deal, but it’s huge. The clowns that drive those trains love, and I do mean love, to blow their horns. Some of them seem to like to try and play little songs by varying the horn as they pass buildings. All very cute at first. Not so much day after day. There is no way I’d live within 2 blocks of the train tracks. Let me repeat… NO WAY I’D LIVE WITHIN 2 BLOCKS OF THE TRAIN TRACKS!!!
2) k, now that we’ve got that behind us… Parking is an issue. There is very little parking down here and if you like to have friends over you should think about where are they going to park. And where are you going to park if your condo doesn’t come with enough spaces?
Lastly, I’ll just mention that Little Italy is nice, and cute, and what have you, but I lived in downtown Chicago, and this ain’t anything like it. It’s okay, but it’s more just congested and inconvenient. There isn’t a grocery store around, and there really aren’t that many places to go out to. Most are tourist restaurants. (Mona Lisa does have the best sandwiches in San Diego though)