Douchebaggery, indeed. In my experience, the people who get tweaked when someone like DHH expresses a strong opinion, are usually the same ones to suck the creativity and excitement out of any room they enter. Unless you're planning to work with DHH, what do you care what he thinks about your laptop? Learn to deal.
It's not a strong opinion. He's saying something stupid and stupidly arrogant:
I would have a hard time imagining hiring a programmer who was still on Windows for 37signals. If you don't care enough about your tools to get the best, your burden of proof just got a lot heavier.
Whatever. I could find you some old fogeys who wouldn't hire you because you didn't love OpenVMS, and Richard Stallman himself doomed us all to using Unix instead of VMS, which he prefered, because of political constraints. Is DHH using OpenVMS? No? Then he's not using the best tools, and he should seriously consider firing his stupid ass.
That he thinks that ability really corresponds to making the polically correct choice in OSes really says more about his hangups than his discernment. As for OSX, it frankly strikes me as the Disney Corp. of the OS world. But that's just my stupid opinion, and I wouldn't hit someone over the head with it.
I code on Windows, and deploy to Linux and have never noticed any differences besides file path names and a mysteriously superior performance of MySQL on linux. Hey--I know linux in and out----why am I not using it for a desktop machine? Because Windows is better at that.