I think if you're openly soliciting donations under the premise that they're essential to keeping the project running at all, you can put up with the people you're trying to get money out of asking questions to ensure that the money you're asking for really is as needed as you say it is.
Especially since he is almost always technically correct--the best kind of correct.
What OpenBSD foundation really needs is a tactful and charismatic person to act as firewall and pf between Theo and the people with overflowing bank accounts, who are more accustomed to dealing with obsequious salesdroids than a person who is not only ten times smarter than their entire golf group put together, but also so aware of it that he cannot hide how much of a waste of time it is for him to suck up to any one of them, no matter how much he could use the cash.
Do you think Apple would have gone anywhere if Wozniak was the one talking to all the investors?
No, what OpenBSD needs is a broader FOSS community that doesn't turn every bump in the road into a referendum on bruised feelings from years ago, and recognizes its indebtedness. I type 'ssh' how many times a day?
Not that I don't understand those feelings. I've spent enough time lurking on openbsd-misc to have seen Theo and friends be beastly. But never without some provocation. And one might wish better impulse control on any number of online personalities.
(And if you find this rude, note that I'm not involved with OpenBSD -- not even on the mailing list anymore -- so blame me, not 'the OpenBSD community'.)
"I really love how we keep getting advice. Anyone want to suggest we hold a bake sale?"