I like the subscription idea. I'd love to have every release without actually doing the shopping every time. This could at least make a bit of safe money.
I believe, making a company sending 20k$ every year to openbsd could be quite difficult. Why should they do this ? What do they get ? Why is that better than spending that money in new hardware or buying fancy whiteboards in managers office ? I know what they would get, but they dont. How do we make a company to know about the benefit of openbsd? They never heard of it. They wont ever use it because they dont get a 24/7 support contract from a big consulting company for it. They dont know about openbsd and most dont care. That might not be the opinion of most people on this list but it is the opinion of most people not on this list [the ones with money].