I don't know how or even really if it applies, but the phrase "too clever by half", and in particular the article that has appeared here several times before [1] came to mind.
Also a thing I've thought about, which is echoed in the opening bits of the article, is that many people will buy or build a starter home, and then over time build it up into something much fancier or larger. At which point, it isn't really a starter home anymore, and who is going to want to buy such a thing when they could just do the same over time except in the style they actually wanted?
It's always entertaining to look through the older Zillow listings for moderately to very expensive houses. Without fail they are testaments to bad taste. They'd cost a sizable percentage of the purchase price to renovate. Yet, the owners just keep holding out hope that someone with equally bad taste will eventually come along and snap it up.
Also a thing I've thought about, which is echoed in the opening bits of the article, is that many people will buy or build a starter home, and then over time build it up into something much fancier or larger. At which point, it isn't really a starter home anymore, and who is going to want to buy such a thing when they could just do the same over time except in the style they actually wanted?
[1] https://www.epsilontheory.com/too-clever-by-half/