I have to say, after living my whole life within 50 miles of the place and having lived and worked there for long periods, that I both cherish and despise NYC equally. It's that kind of city. God knows i can't afford to live there anymore... well, I could, but I don't want to spend 80% of my income on rent. etc.
Hoboken, NJ, the "Mile Square City" was really nice when I lived there... post-recession, but still very ethnic-neighborhood-ish, with loads of parking space and cheap rents.
The real estate boom of the late 80s was very good for a lot of folks in tHoboken, but of course the death knell for the character of that city.
It all went to hell when they tore down the Maxwell House plant- I used to be able to get a caffeine buzz just walking around, on days they were cleaning the tanks or whatever. And it was just an awesome symbol of Hoboken's incredibly industrious past (more people lived there during WWII than do now).
Then the "bridge and tunnel" lunkheads from the western NJ counties started going out to party there instead of "the city" (Manhattan). "Old man" bars, where a guy could cash his paycheck and have a bite and a few beers and shoot some pool, started to vanish. Then rents skyrocketed.
Now it's way too crowded and way too expensive, and if you're looking for a parking spot at any time at all, and there is a car in front of you, you will not get a spot, because they are looking too.
But it still has over 50 bars packed into that square mile (still slightly more than churches), some great restaurants, and very nice little parks. Also, it seems the most beautiful women who work in Manhattan live there.
Went to college in Syracuse, NY- very nice up on the hill, but downtown was pretty uninspiring, especially with a foot of snow on top of a six inches of slush covering ice chunks resting atop three inches of rock-hard ice. With freezing rain blowing sideways at 20 knots.
Winter is brutal and unrelenting there; the beautiful summers just make it worse.
In my travels, I've rarely stayed anywhere long enough for the novelty to wear off, but although SoCal is a bit... weird for this NJ boy, I really enjoyed my 8 weeks in San Diego. The weather, the scale of the city, the food, the surrounding areas... I could get sick of living anywhere, but it'd take me a long time in SD.
New Orleans... forget its vulnerability to hurricanes, and it is a great place to visit. My first time there was when I flew myself all the way from NJ to Lakefront in a 172 and stayed for a week. Can't find a bad meal or a lousy band in that town...and it really is dripping with charm and mystique. I like it. Been back twice since then. But I couldn't live there; I don't have a clue how I could earn a living there.
I wasn't too crazy about Chicago, though, and not just because I've been there mostly in winter...just didn't grab me. But the subway system there is like the Orient Express compared to the NYC system. And you don't have to go far from downtown to find yourself in an unlikely pilot's paradise... I really enjoyed flying out there and the fine pilot-folk I met.
I could go on and on... but I think my personal "worst" prize has to go to the only big town I've visited outside the US: Tijuana. A huge, parasite-infested tourist trap. I'm sure Mexico has a lot to offer, but it ain't there. How good a city it is seems to depend on how drunk you are, but of course the next day you realize it was horrible.