37Signals is making their point heard, but it's not the professional way to handle things. I completely understand the reaction, DHH is rightfully upset. It's usually best to take some time to cool off and then respond when you're a little less emotional.
Just because an emotional response goes against MBA Corporate PR 101 doesn't make it wrong. He can do whatever he wants, and he does. In the context of his company, I'd even say it's a winning business strategy, because it's different and doesn't feel artificial, which is refreshing in this age of sterilized corporate communications, and is therefore memorable.
And there's nothing morally wrong about fighting back against people who have ripped you off.
While I believe DHHs reaction/words are entirely attributable to his passion for his company/product/coworkers, Cynical-Me also notes that this choice of public personality is generating an awful lot of pageviews/eyeballs/comments, and even the negative-to-DHH comments are largely positive about Highrise/37Signals.
If a hughely talented but completely amoral PR specialist had scripted this, perhaps it would have turned out exactly the same way...