That’s my fear - that it just keeps going up. Probably not a good idea to ”gamble” like this. My house is in a great neighborhood and I can afford it relatively comfortably. My other option would be to invest in a second property (house in my city or apartment in NYC, probably my old neighborhood in Brooklyn). Right now, my money is sitting in a cash account, no interest, and I need to do something with it eventually. Not much but still enough for a down payment.

I would not sell my main home and look to rebuy. Just the realtor fee, staging, cleaning, moving will mean prices need to drop 10% or more for it to make financial sense to rebuy. If you have cash, buy an investment property.