Move to Kensington, Maryland where your name is inscribed on a bridge:
The average temperature difference between Indianapolis and St. Louis is about 5 degrees, according to weather.com, so I don’t know about “much colder”.
Don’t rule out NYC. Manhattan is insanely expensive but the outer boroughs aren’t. You could get a room in Queens or Brooklyn for a reasonable price. And you can’t beat the wonderful public transportation. The buses and subways are cheap, run 24 hours a day and they go pretty much everywhere including the airports and one of the world’s best zoos. You could even think about a Staten Island sojourn. The Italian food is great, the view fantastic and the ferry is FREE!
Another vote here for Charleston, SC; mild winters, low cost of living, plenty of jobs and a variety thereof. Tourism being one if its main industries there are plenty of food service jobs and it’s got big city feel on a small town footprint. It’s cosmopolitan, w/ plenty of people from all over the world living permanently there; one hotel we stayed at, the manager came there on vacation from Canada and went home only long enough to arrange emigration. There’s a well-regarded LGBT population, it’s low on the Jesusy quotient for a Southern city that’s full of historical churches and the ‘farmer’s market’ is simply a year-round market downtown that’s closed about 7 hours in a day from what I can tell. There are stands of fresh produce and seafood along most major roadways all over the county.
If you wanted to, you could live all year on a boat in Charleston.
You have to want to be bored living in Charleston, even if you’re broke. It has decent transit as well. And dolphins. Chicago, Austin, Philly and Indy can’t offer you free-living dolphins, just swimming around their rivers, doing dolphiny things.
I would love to know what is considered reasonable and what is included in that price.
Another vote for New Orleans. I’m a cook here and got a job fairly easily. There should be a ton of restaurants hiring when the tourist season starts heating up in fall. Housing is also super super cheap. You can get a 2 bedroom shotgun house or “double”(like a duplex) for under $700 a month in a not-horrible neighborhood, and split it up with a roommate if you want it even cheaper. Then you can have dogs and have a little yard for them. Much better than a studio apartment. Yeah, there’s always the risk of a hurricane, but in general, the weather is really warm and enjoyable all year round. People who grew up here are pretty nice and friendly and there’s enough fresh blood from transplants to not get too insular.
Our nightlife is pretty awesome. There is about a bazillion places to see live music and they aren’t all Bourbon Street tourist traps. As a restaurant worker, I appreciate the fact that I can get off work after midnight and the bar will still be open and poppin’. Most people are fairly tolerant of GLBT people, at least more so than anywhere else in the South that I’ve been. New Orleans has a strong Catholic heritage, so people don’t try to proselytize you as much as places with more Evangelical Christians. The vegetarian thing might be a problem, because almost every delicious thing in restaurants has some kind of shellfish or pork product. If you eat seafood you will be fine though.
I’m not sure about the rest of the city but you can rent a room for $100-$125 a week in Manhattan. You can find a roommate and split the rent in a 2 bedroom apartment for $650-$700 per person/per month or find 2 roommates and a 3 bedroom for $500-$550 a month per person. Each apartment will have wildly different things, some have a washer/dryer and a dishwasher and some don’t, some are right next to a subway stop and some aren’t, etc. I would assume that the prices are a bit lower in the rest of the city. The public transportation is cheap so you can deal with the higher rents by not having car payments, car insurance, buying gas, etc.
Thanks… my question really was serious. More reasonable than I imagined. Still expensive by Midwest standards, but not as bad as I thought they would be.
Just to take this scenario as an example. I worked in real estate in Manhattan for one year in 2004, exclusively in rentals. I saw plenty of three bedroom apartments for around $1500 then, and they were all tiny, rundown dumps. ALL of the them. I wouldn’t want to think what kind of three bedroom apartment $1500 would get today in Manhattan. Hey, for all I know you can now get a palace for that amount, but I strongly advise anyone who thinks they can live in a decent apartment for that price do some serious research before you get your hopes up. No offense, pbbth, but that’s just my experience.
Let me add that if you go all the way up to Inwood, which is still of course technically Manhattan, you might find something up there. I had no experience that far north…
So, maybe what I was thinking of as a $1500/mo 3br isn’t quite what pbbth was talking about.
Here is what you can get in the Midwest for a little less than that.
And at least if you have to have a car here you get a garage included at that price.
I find it hard to believe that one can get a room for 100-125 a week in Manhatten. It was almost impossible to find that in Chicago, the best I could get was 150 a week in a ghetto neighborhood or Uptown. And those rooms would be infested with mice and have no hot water. And I know SROs are disappearing all over the place. Good luck with that!
I agree. In 1994 I moved to a weekly room with a shared bathroom in Queens, with a shared bathroom and no kitchen facilities. It was $75 a week if I remember correctly, and that was 18 years ago. In other words people, don’t get your hopes up living decently in Manhattan on the cheap.
Ugh. All I have to say about that place is…ugh. The Fashion Mall is the most traffic-infested area of town, and for that price (the 3 br), I could get a mortgage on a house twice the size of my current home (1800 sq ft).
Oh, I agree… my mortgage on a 4br house is about half that. It was just the first one that popped up on a quick search for 3br appartment under $1500/mo. Just using it as a point of reference on what that price point gets here. And even though you and I know what a headache it would be to live there, there are tons of people scrambling to get there because it is “fashionable.”
I worked for Citi Habitats during that year in 2004. They are one of the biggest agencies in NYC and cover all of Manhattan, with a fair amount of listings in the outer boroughs. That link is to their rental listings, if anyone is interested in what $1500 will get you these days. Currently they have exactly one 3 bedroom apartment at $1800 per month in Manhattan, and none cheaper, so, yeah, good luck with that. 
I will say for the record that it actually looks livable though.
ETA: I should add that the listings at the site are just the ones agents decide to post. There are surely others, but agents don’t generally put up links to the dumps, but oh the stories I could tell you about them. You don’t want to know.
You mentioned Austin, but San Antonio, TX also fits your bill - plus, Austin is only 60 minutes away and you won’t have to fight that horrible I-35 bottleneck in downtown Austin every freakin’ day. (Seriously, for a city of “only” 800k-odd people, Austin has some tremendously shitty traffic).
Get out of St. Louis. Your jobs outlook is quite horrible - 14% of employers look to hire more people, but 12% of employers are expecting to lay off people. Worst Cities to Find a Job - Business Insider
Compare that to San Antonio (22% hire, 8% reduce) or Austin (21% hire, 6% reduce)
Some of the cities mentioned in this thread belong in the “best to find a job” category, including Charleston, SC and Asheville, NC.
New Orleans is also another city where hiring is expanding. But it’s hot and muggy (though St Louis is as well…)
I guess Asheville’s not that expensive. It made the list of Most Livable Cities In Bargain Markets, as did several of the other cities mentioned in this thread.
Actually, I really do. Do you want to start an “Ask the…” thread? 
I’ll do Portland – I like it well enough. You won’t be able to find any books – the public library is small, and the local universities don’t have basic texts for doing any sort of work in the humanities, except maybe if you’re an undergraduate trying to pass some humanities course. And it’s a dinky little cow town with a lot of hipsters, and a bunch of shitheads riding their dumb bikes. No art museum to speak of. No jazz club.
But, you can spend a day walking thirty miles in Forest Park without driving out of the city, and not seeing the same tree twice.
That’s a big sell, and it’s the reason I like it here.