Bay Area is insane. I pay $850/mo for a 4B/2BA house in upstate NY.
I work locally and telecommute now, but I used to commute regularly to the Boston and NYC metro areas with commute times similar to what I hear about from some colleagues in the Bay area. 2 hours on Amtrak (+10m drive) is much more pleasant than 90 minutes in the car to me. The haul to Boston was truly awful, but the pay was too good to pass up.
Wow! My mom lives in a small, dated apartment in an unexciting suburb of Rochester away from colleges, with paper-thin walls and ceilings, and pays about $1000 in rent. That seems standard for the area. About 20 years ago we paid $650 a month for a tiny two-bedroom. How does your upstate New York cost less than one fourth of that?
Rents always suck upstate. A two bedroom in a nice development in a suburban town near me is about $1400/mo. Ownership is always cheaper.
As for the costs -- I cheat a bit. I've been able to build more equity over the years and refinanced into lower LTVs as time and rates went down. I bought my first house as a student at a SUNY school -- my mortgage was about the same as a "student ghetto" apartment. This house I bought about 15 years ago. In my urban neighborhood, houses sell for about $135 sqft today. In the suburbs, it's about 30% more, and you are basically paying for better schools.
You can get a small, nice house in a place like Fairport, NY for $150k. I don't know that area super well, but you might find lower costs in an adjacent county without the tax/infrastructure burden of Rochester.
I work locally and telecommute now, but I used to commute regularly to the Boston and NYC metro areas with commute times similar to what I hear about from some colleagues in the Bay area. 2 hours on Amtrak (+10m drive) is much more pleasant than 90 minutes in the car to me. The haul to Boston was truly awful, but the pay was too good to pass up.