Chip,
It sounds like Matt doesn't care if you sell themes, plugins, or whatever as long as you don't try to do it on WordPress.org.

Obviously however, he is willing to display your themes on WordPress.org if you only charge for support and the theme itself is free.

Why doesn't Matt realize that this will ultimately lead to consumers not trusting the designers? What is going to prevent a designer from designing a theme in a way that it REQUIRES support in order to use it?

And why would a designer choose such a business model when it would require more work on his part to just provide support? That is, he could make just as much, and realistically, probably a lot more money, selling the theme and not providing support. I mean once you build the theme, it's done; you sell it and make money. The only time required is the time it takes to build it and advertise. If you are only going to make money by supporting it, it's going to take a lot more time, expenses, and your earnings potential will be much less because support requires hands-on paid work which is also a limiting resource. Selling a theme however, really doesn't have a limiting resource except for your ability to advertise it I guess. Hence, I don't see designers adopting this service based business model any time soon.

Which reminds me...why is the Rev2 ad on WordPress.org no longer there? Did Brian Gardner bail on the whole "Premium Open Source WordPress Themes" idea?