Hi Matt and everyone
This is a very good discussion to be having. I've been considering these licensing issues for myRadio, in a very similar way, though not as much depth. So, it's very cool.

A few scattered thoughts, on licensing and business plans.

+ myRadio is designed for extendability by other developers. I'd like to see an "extendable" license, where use of the bundled tool set is covered by the same license. This could also work for tools that myRadio integrates with (like aR) and non-myRadio tools - for example bundled together in an enterprise solution, as has been discussed with evectors. Of course, these tools will be free to enforce any license of their choosing if they wish.

+ There's great potential in the bundled enterprise solution, from a marketing perspective. How would fees be distributed? And how would a single registration for a set of tools be implemented?

+ Licensing to Userland would be brilliant.

+ Definitely solicit donations. Without even asking for it, I have received donations for myRadio. Super cool. At the moment, I am only working for myself, by semi-choice. Donations are a great motivator, though not enough to survive!

+ Any registration scheme is easily defeatable in Radio, because of the open code. Yes, portions of source code can be removed for distribution, but unless the entire tool removes source code, there is always some place to defeat this protection. Is this a worry?

I am out of my element when it comes to monetizing the technologies, so any suggestions, for myRadio and others, are welcome.