If you’re worried about the heat in San Antonio and Austin, Tampa probably isn’t a very good idea. Although temperatures don’t get quite as high during the summer, there is a lot of humidity, so it feels much hotter than it actually is. The winters are nice though.
Actually there are some very cool neighborhoods in L.A. if you like living in a mixed commercial-residential area (i.e., there are a lot of restaurants and things you can walk to). If you’re ever visiting out here, check out Larchmont Village, West L.A. along Santa Monica west of the 405, Beverly Hills, and various parts of Santa Monica.
Houses are very expensive here, but apartments aren’t too bad if you don’t mind being a renter.
“Los Angeles” is a somewhat nebulous term – while technically it refers to the city of Los Angeles, most people (including myself) use it to refer to the entire Southern California basin, from Santa Barbara down to Long Beach – maybe Orange County, too, if I’m in a good mood. 
Yeah, there’s a lot of sprawl, but that’s part of the appeal, having more room to relax. Cleaner than Chicago, more cosmopolitan than New York City, more affordable than San Francisco … the only people who diss L.A. are those who are jealous they don’t live here. 
Montreal. As close as you can get to Europe without leaving the continent.
No one’s mentioned Minneapolis? I was there this past September, and thought it was one of the better cities that I’d visited. It does get cold in the winter, but it was in the 70’s when I was there. Damn near perfect weather. DoctorJ, I feel your pain. I live right across the Ohio from Louisville. I’ve personally always loved Chicago and Atlanta.
Too bad Santa Cruz, CA is too small for you…I’ve been here for three years and it is literally heaven on Earth. It is filled with beautiful redwoods, wonderful beaches, interesting people, nice weather (think a sunnier San Francisco), a strong sense of community (for example, few people shop at chain stores) and a genuine California laid-back attitude. The only drawback is it is about as expensive to live here as it is to live in San Francisco.
Do your residency in Dayton, Ohio, and live in Yellow Springs. Dayton is a nice, middling city which seems to be about the right size for you, plus there are some decent residency programs. And, not ten miles outside the city limits, is the most interesting town I’ve ever been to: Yellow Springs. Looks like someone took a cookie-cutter to Haight-Ashbury circa 1965, lifted it off the globe, and dropped it in a woodsy area in otherwise unremarkable southwestern Ohio, where it remains preserved in its free-spirited but modest state lo these 35 years. You want personality? Yellow Springs’s town motto is “Personality”. I encourage you to drive up there and hang around for an afternoon. You’ll think you’re living on the cover of a Moby Grape album, only without the pretension and degeneracy that killed the counterculture everywhere else.
Boston is pretty groovie. gets a bit chilly in winter. great pubs, good shopping, fantasic seafood.
Boulder and Denver are good places to live. Good people, great food.But housing in Boulder is really expensive.
I love Sydney, AU. We’ve been here for 4 years now and I don’t wanna go back to the US. It never gets cold enough to snow, everyone gets 4 weeks paid vacation per year, beer drinking is a national pastime, and best of all NO PENNIES!!! I know, I know, but it’s the little things…
Gets plenty cold enough for me. Brrrrr-r-r-r. Geez, I hate winter.
I’ve lived all over the country, and right now I’m in St. Louis, which is by far the best city I’ve ever lived in. It’s like a middle ground of everything. Summer and winter both is rather mild. I live in one of the highest class areas and it is comparable in price to a middle class area of So. CA, which I moved here from. It’s a great mix of country and city. I live 10 minutes from 3 malls and still have deer and other critters in the yard. The people in general are a lot friendlier than in CA. The traffic, even during peak hours is not that bad. Rush hour here is called rush hour in the literal sense. During my work commute, I average about 75mph and I’m usually one of the slowest cars on the road. The crime rates are lower than most other major cities. As far as your line of work, I’ve been very impressed with the hospitals here. Some of the other cities mentioned here though, I do have to give honorable mention to like Santa Cruz (probably the most laid back city in CA), Atlanta (gorgeous city), New Orleans (can’t beat the food and the people), and Minneapolis (I’m a native MN person so I’m biased, but the winters can be a bit harsh for a southerner). I spent over 15 years in the LA and Orange County areas and it would take a large, six figure salary for me to even begin to consider ever moving back there.