>Relatively crappy homes in town that were 100k back when I was looking are now north of 250k.

We'd need to know more about your area to really assess this... $250K really isn't very much money. In my area, you could afford that house on our minimum wage, even as just a single-income household. In fact, the mortgage on it would be less than our typical area rent.

I hear a lot of stories like what you are sharing about the beautiful 60 acres back in the 80s... let's just say that baby boomers for all their complaining about 18% interest rates actually had a whole lot of things working for them that we don't today. Competition is different because capital moves around the world easily.