No one has a crystal ball, so it’s a question of odds. With that, here are my thoughts.
If you want to give yourself the best odds of the best financial outcome, then you should wait. All the negative factors that hit the lower end of the SD market haven’t percolated through to the high end yet. (A few people here think they never will but, as I said, it’s a question of judging the odds…)
Psychologically, it’s a completely different story. Most people who bought houses in the last few years paid with what I will call “Monopoly money”. That’s why they could bring themselves to write a check for $1 million for a dumpy place. For every 100 people who wrote that check, there were only a few who had actually saved most of that money by spending that much less than their net earnings stripped of capital gains. Most of the others borrowed most of the money, expecting to pay the loans back painlessly from a higher future sale price, or they used prior gains from previous home price appreciation (“equity”). It was therefore easy money, and they spent it more freely.
Based on your comments, I am guessing that you have a large pot of money for this next home purchase, and a lot of that money came for substantial prior home price appreciation. Each $1 of your housing pot didn’t come from a $1 saved by scouring the supermarket shelves for good deals, or taking cheap vacations, or some other self-denial. It came from high previous asset price appreciation, which was pretty painless, so it “feels” OK to spend a lot of it without counting the pennies.
With that (cheap, and worth every every penny) psycholgical profile, I’d say that you should just find a place you like, and make sure that a loss of 30% of the price would not exceed your prior gains.
