Very risky proposition trying to play the market as u/Peeeculiar said. Real estate crashes are not universal. Around major cities they tend to be dampened. Southern NH/Boston area may not really crash, even if a lot of other places in the country do. Even in 2008 there was not that much of a crash in local prices. With more people wanting to move to NH, more work from home, and inflation going nuts, I really can't see home prices going down all that much. I'd have to say your friend may very well be regretting his decision in a few years.