> If I choose open source, I don't have to think about licensing, feature matrices, or recurring billing. I know, I know, we don't use software that costs money here, but I'd almost be willing to pay for the privilege of not having to think about that stuff ever again.

The grass is always greener on the other side isn't it? Don't get me wrong, FOSS has upsides, but segmentation isn't one of them. If time really is the cost rather than the cost of the software, FOSS isn't any better. The only difference is that nobody is artificially segmenting the market. The market artificially segments itself.

Think about it: do you use Debian? Fedora? CentOS? Or do you go with someone you can buy a support contract for like Red Hat or Novell or SuSE? Or would you rather go for a BSD flavor of nix? OpenSolaris seems to also be gaining popularity; do you choose it?

And once you get that sorted out, what webserver do you choose? Apache? Lighttpd? Nginx? Comanche? Are you doing Python? Then you also should consider CherryPy.

So, to summarize... sometimes I'd be willing to pay money to know that no matter what* edition I choose, I'm still buying Windows.