I think I understand what you are asking which is, to jump into some of the stock that may have been built in the 70’s and 80’s now (or in the near future) verses waiting and purchasing some of the stock that is maybe less then 10 years old.
So I think that the question is subjective because my own personal purchase is taste driven. For instance for me personally I want a larger lot, no recurring costs such as MR and HOA, (though if need be I would tolerate a small HOA) and spacing between my home and the neighbors. Those factors alone filter out most housing, (that I can afford) built in the last 20 years.
While it is true that some of the older stock you have referred to is less expensive then the newer stock, I tend to think both types will depreciate in an equivalent manner. It could even be argued that the newer stock could fall a bit faster and harder as one may speculate that these purchases were made more recently and thus prone to distress. This is an arguable point. Both newer and older homes also are subject to wishful analysis where sellers list with the highest offer quoted by an agent. There is a home that hit the MLS less then 10 days ago in Carlsbad that I visited with, (a perfect example of an older home just blocks from newer homes). They didn’t list with me because my price recommendation was lower then what other agents told them. When I showed them the data I used they understood it and when I asked why they felt the other agent could fetch a higher price using the same comp data they said the agent told them there are many cases where homes sell above comps. Perhaps they will get the higher price that the listing agent recommended.
So I guess my answer is not really anything concrete with respect to new verses old. If you are finding that your price point of what you can afford only permits older homes due to the price point then I thoroughly understand. In many parts of Carlsbad though, I can see pricing coming down in the next 2 years of alot of the newer stuff given no (more) federal intervention of which I am becoming more and more concerned with. Yet if you are really considering buying now then yeah you may get more square foot for less money with the older homes. Both new and old will fall though.