(wife of OP here)
The home purchase will occur in the next 2-3 months. The plan is to stay in the house 5-10 years, but who knows? We're switching jobs and moving to a new area. It could be a total dumpster fire, in which case we're looking at ~ 1-2 years. FIRE isn't far off for us, but we'd like to give the new jobs a chance, because they could be really rewarding. Plus we FINALLY made it out of the frozen tundra of the upper Midwest, and we're working on being happy here on the east coast.
The NYT rent vs. buy calculator is in favor of buying, because 1) rentals in this area suck 2) we have a substantial down payment available 3) we're projecting 5-10 years of ownership. The NYT calculator doesn't figure that the things that make us happy (quiet, our hobbies) can't always be had in a rental unit. But we've been watching the market for the past three months or so, and it's stupid. Just stupid. Offers go in after only a day (or less) on the market, and they're well above list price. The article referenced in the original post reveals that buyers are writing letters again to form some sort of emotional bond with the seller: echoes of 2006-2007. Will the market "crash" as epically as it did in 2008? No, probably not. But paying $550,000 for a FIXER UPPER is insane. $700,000 for a 1900 sq. foot, 60 year-old ranch?
We'll probably settle on a compromise: a 2-3 bedroom something-or-other in a quiet area that might need some work. Something we can live in happily enough while we figure the rest out. We'll probably take a loss if we have to turn right around and sell in a couple of years, but a loss on a $270,000 home is easier to swallow than the loss on a $600,000+ plus home....all the granite countertops and hardwood floors couldn't soften that blow.
Buying now doesn't feel nearly as comfortable as it did when we bought our first home in 2013, despite a much larger 'stache and way more knowledge about the trials of home ownership. We're just commiserating with people who are thinking about buying now, too.