I use "crappy town" to mean that it's not where the masses live and it doesn't have any of the usual attractions, ie it's crappy to the mundane generic taste of the 95% of America that chooses to live in metro areas.
But if you aren't looking for the usual attractions, then a crappy little town can be, as I said above, perfect. I've lived in a few myself, and spent plenty of time visiting and considering many more.
A house selling for less than $500k is unheard of in NYC and LA. In NYC, you can buy a studio apartment for $300k but then the monthly fees are never cheap and never paid off.
A decent house in a no frills but safe neighborhood for less than $75k is hard to find in most cities around the country. Under 50k for a 3br house in good shape is unheard of.
And they don't happen in places with strong economies. When you see them it's always in the ravaged neighborhoods and bad parts of town. In a city, cheap housing will exact a toll on your soul. In small towns, it will consume your life commuting, as you'll usually have an insane commute if you still want to hold a job somewhere.
Plus, even though I lived in some of the hardest hoods in Brooklyn for years, the idea of putting on bright tight clothes and tooling around on my expensive bicycle in the hard core parts of Detroit... definitely gives me pause. After all, I wasn't doing the Brooklyn thing in the 1980's pre Guliani urban warfare era of NYC. If I was, I doubt very much I'd have been out dressed like a skittle on my bike.
So if Gainesville is an OK area, then that house for $45 is a bicycling retirement dream. Near the mountains, near the lake, and a relatively nice house. If I wasn't holding out for the dream of LA eventually, I'd be driving down to check out Gainesville this weekend.