Austin. For a laundry list of reasons:
1. No sense of community. It's one of those places that touts how great it is and claims being friendly when it really is all superficial and exterior. It is so hard to build a social support network in this town centered on something besides amateur music and cannabis. I work for a suburb 16 miles from downtown and I've come across way too many people in central Austin who have no idea where it is. This sort of lack of knowledge/shared sense of place I don't think can be found very many places. To top it off, they're snooty about it in a way you don't really see outside of New Yorkers never leaving Manhattan, Clevelanders never crossing the Cuyahoga, suburban Detroiters never setting foot anywhere between 8 Mile and downtown.
2. There are two freeways to get downtown, I-35 and Loop 1 ("Mopac") and both bottleneck (shortly) after being intersected by US 290 and US 183. Traffic is a nightmare for so small (relatively) a metro area (~1.6 mil). It has taken me 3 hours to get across town (from TX-45 to Kyle) before.
3. U of Texas students, as a whole, are dumb. Like don't-know-how-to-order-off-of-a-menu dumb. That being said, I've met a lot of nice, intelligent people who have gone to school there and who are current students. As a whole, the description applies. And, outside of the state history museum and mediocre art museums and symphony, there's no culture in Austin outside of UT, unless you're thinking of pot and/or amateur music. Once you're out of your youth, Austin doesn't have much to offer.
4. Upward economic mobility is practically non-existent. You'll progress to a certain point and then hit a ceiling. Some friends have expressed comments akin to "Austin is where dreams go to die." It also traps you in town and makes it hard to get out. Very few employers seem to respect work experience received here unless you're state government employees, and even then... it's Texas.
5. There is no good urbanism here. I realize this is not an Austin-specific problem. I just find it that much more aggravating when people adamantly claim non-NIMBY status then kill any good project in their neighborhoods.
6. Incredibly pretentious. I'm talking rivaling the Bay Area, here. Combine the uptight liberal attitudes seen in San Francisco (nothing personal, Bay Area residents and natives) and combine it with the Texan arrogance.
7. The primary culture here is a mixture of "Stuff White People Like" hipsters, hippies, and cowboys. It might sound intriguing, but really just amounts to activist hippies with western clothing and accents.
There are good things about Austin, too. It's pretty well integrated, racially (I wish I could say the same socio-economically), the area around the city is one of the few truly pretty scenic regions of Texas, the weather is generally pleasant 10 months of the year and sunny all year, an active downtown, the cost of living is relatively low compared to the rest of the country (but not Texas, unfortunately), you're within 3 hours of 3 of the biggest cities in the US and two of the largest metro areas, so whatever your sports/music/culture interests, if there's nothing in Austin you're pretty close to just anything you might want. But still... if I wind up here for the rest of my life, I'll probably wind up pretty miserable. I just want everyone to know that Austin doesn't fall anywhere near all the hype surrounding it. It'd probably be a fair college town, where you live for 4-5 years for undergrad, but afterward leave for bigger and better things. But as an end destination unto itself, it's falls way below the bar they've set and paid for others to set for themselves.