Bottom line is no one knows really. You’re question is the answer. There are too many factors to really determine the outcome. In some areas, the actual dollar price will decline as well as have inflation catch up with it. You’ll spend more dollars that are worth less, but easier to come by on a house that is worth less after adjusting to inflation.
So yeah, in some areas, a house that was $200k in 2000. Will sell for $400k in 2008, but will actually cost as much if not less than if the house was purchased in 2000.
Chula Vista, Poway and Downtown SD will likely get hit the hardest here in SD. Older hoods will probably hold some value in terms of the actual price (but it they will be devalued because they will not increase with inflation).
Chula Vista is over built, Downtown is way over built for the market (young single realtors), and Poway is Poway. It’s a long drive to anywhere and everywhere and there are not enough freaked out white people to move there anymore.