I know I am new here, but here are my two cents ;D
I am for open source and commercial modules, themes, and all that. You can always open new section in this forum for commercial stuff, and developers can post there stuff there and also support them right there ( that is a new concept, right? )
I think that for now all modules and themes should be free, until PW builds its own community.
Ryan, you can always make specialized modules/themes (commercial) for specialized fields. For example: There really isn't any good CMS or system out there for photographer portfolios. And the one what are there are way overpriced or to complicated that you need degree in engineering to upload your pictures to a gallery.
You definitely should have enterprise support. Its always good to know that there is a help when one needs it. ;D
You can also have section in the forum "hire developer" ( another brilliant idea )
Wish you well