I'd also be interested in following up, publicly or privately, in a more direct way. I support what you're doing, and it sounds like you support at least the spirit of what I'm doing. We should talk.
One point I'd like to go ahead and bring up:
A common thread through the examples of success you've given is size. There are some examples of single-person, profitable operations, like Sidekiq, but they're very, very rare. Many successes boil down to economies of scale on services, information, relationships, corporate process compatibility and so on.
L0 aims to make one business model that currently involves a lot of structure---dual licensing---available to very small, independent players. As an indie developer today, sure, you can set up an LLC and start e-mailing forms off the Internet to procurement departments. But doing all that will swallow you, as well as the time you already don't have to spend developing software.
Part of making that play available to indies is automation. Part of it is standardization: one form for buyers to review. Part of it is network effects: one place for customers to get all the licenses they need, in one transaction. Part of it is recognizing a play that can, forgive me, "scale".
Dual licensing is the most direct of the well known options, in that sense. The software is valuable. Pay for the software. Where does the pay go? Into the one who'll make more and better software.