As much as we'd like to ignore it, there is more to a working relationship than technical issues and philosophical issues. Nobody wants to listen to a person who is perceived as being both unduly critical and pugnacious about it. Yes, image matters.
OpenBSD and the other software projects that fall under that umbrella are nearly universally noted for their security and technical correctness. But Theo himself, in contrast to the positive things he contributes by way of his code, is most often heard praising his own projects yet, in the same breath, cursing Linux and other things that side of the BSD-GPL divide. Usually, people who seem to act like this do not attract money given of free will.
It really doesn't matter how factually wrong I am, because it is a matter of perception. I perceive Theo as having a generally unappealing personality, and I assume that many others have similar sentiments. This is to be contrasted with someone like Linus, who is widely seen as having an appealing personality.
If he is to be the one to garner support for the projects, then this perception must be challenged widely. Given the audience, facts are likely to carry more weight, but it's still fundamentally a PR battle.
Just saying.
