Ahhh Cliff that is the golden question is it not? My personal read (which is simply an opinion) is that things will stretch out longer then that. Left to its own devices I think the market would fall quicker and normalize quicker. Wildcards include a potential recession and in my opinion the bigger wildcard will be how we deal with the economics of a falling dollar. Sometime in the future the piper will be paid and interest rates will go up and if they go to where they need to go, that could have a much more whopping on the market then what we have seen in the past 2 years.
Also I think what you said is particularly true about your target market. It is supported in a heavy manner by working class people with strong jobs and 6 figure incomes. I do believe it will depreciate but where the bottom is nobody knows. Many will speculate it is another 30%, 50% perhaps more. I am not in the camp of a 50% depreciation but over several years I could see an aggregate of 30%, maybe a bit more or less…
This is probably the most discussed topic on this website, how far down will desireable areas go. You already know that correct?
Also if you are planning on buying, and it is for the long term of retirement then you can look at it two ways… One, that regardless of the price, if you are secure you can make the payment, then you are good regardless of the roller coastering of the market. Conversely, you can say, well, if I am buying for retirement, what is the rush? Why not sit tight another 2 or 3 years, and potentially save alot of money. Family harmony is important as well but I get beat down by the bears whenver I mention that so I will not harp on it…
Like you said, in the rearview mirror a few years from now you will know the answer. All you can do in the meantime is run numbers and see what they will look like so that whatever you do, you will not run into an unexpected event.