How much of that is just "contrarian as a marketing tactic"?

IMHO, all of it. The real winner is whoever they bought "Once.com" from, good for that person =)

Sadly it works and here we're talking about it.

But yeah I agree

It's exactly that. Jason and DHH have built their entire personal brands on contrarianism. It works for them, but at a certain point it feels inauthentic.

It's 100% not authentic. I have worked directly with one of the two you mentioned and it was an awful experience. The way they treated people around them (both people they knew personally and people at the company I worked with them at) was awful. Based on my experience with them I have never used another 37 signals product.