I'm really indecisive when it comes to housing. I've been in my condo for twelve years. It's fine. It isn't great, it isn't bad, it's just fine. I don't want to retire here. I also don't want to buy an expensive house that saddles me with a miserable experience. I end up browsing real estate websites looking at sort of cheap houses in nice neighborhoods.
There's one built in 1930 that fits the bill. It's two bedroom, one bath, with an asking price of $250k. It sold for $165k in 2012, but I think the current owner did some improvements. Current pictures and older Google Street View show skylights were added. While I'm annoyed it's 50% more in six years, it might still be worth it. 1930 makes me a bit cautious, but I might just be making excuses to accept status quo.
I sometimes think I'd like to live out of town, but I'm not sure that's practical for someone single with no kids only because of the risk of future medical issues. What if I can't drive myself to a checkup? Or if I can't plow or even walk up my own driveway? I drove past a beautiful lot for sale. Wooded and hilly, and at my current age no problem. If I was 70? Maybe a problem.
I go round and round on this.