I have my eye on a place that I love, is within reach, and I would feel lucky to get, but I would have to kinda reach to make it work. It's a very high COL area (Boston), but it's one of the rare places within reach that I would really enjoy living in. It's slightly over my 30% of gross income (if I opted to work a few hours extra each week, which I could do, but wouldn't love), and I would have to put a very large downpayment down. (I'd be left with 40k emergency fund, a little over half of my yearly income worth). I know that lots of people in my position who would pull the trigger just to become part of the increasingly-rare group of milleneals who own a place that they enjoy. However, I know there are probably wiser areas to spend my hard earned money from a financial perspective. It's one of the worst times ever to buy a place because both the prices and loans are simultaneously overpriced. At the same time, you could make the case that buying a decent place in a good area is an opportunity not to pass on, and if you could make it work, you should make it work. Obviously it would make it much easier if I could predict the future about where prices and rates will go, and about what will be available, and how much money I will earn in the future. But since I can't, I feel conflicted about where to base my decision. It might help hearing from other people in the market or in similar predicaments about what goes into their decision.