Thanks for the replies. I've already figured out the max I can comfortably afford and have been preapproved for a VA loan based on that amount. I'm feel like I have a pretty good idea of what I can spend and factor mortgage, HOA, and taxes when I look at a place. I would rather buy a house, but I have yet to find a sf house in my area (greater Boston area) in my price range that's not a "handy man special", and I don't really have the time nor the know how to take on a project like that right now. I guess what I'm really looking for is people with horror stories about bad neighbors, poorly run associations, general maintenance of a home, etc.