I'm mainly curious about this from the context of primary residence, but it might make more sense to view it at least partially as a real estate investor. This question is really about when the price delta is largest between big and small homes.
Let's say that you have the money for one giant mansion, or, alternatively 5 small single family residences in the same vicinity. You decide that during really hot markets, you are going to choose one of those options, and when home prices soften, you will switch to the other option. Given that choice, what would be the best way to maximize return on property value (ignoring rental income)? Should you buy the big house when prices are up or when prices are down?