Jason's post was great to read and I'm glad that it has given you some inspiration. I'll echo everyone else's comments and say that I think you have what it takes to strike out and really make something out of your love for WordPress.

You've got a lot of great ideas and you've got your fingers in lots of pots, I think you just need to sit back and focus on what you really want to be able to do (and on what aspects are most important). Setting clear goals, at least for me, always helps.

Also don't sell yourself short when it comes to getting ads, WordCamp sponsorships or WordPress Weekly sponsorships. You have a broad reach and you are a connected part of the community; you can charge accordingly. Looking at your ad sheet, you point out numbers like RSS readers and forum members but not demographic information about who listens to your show, calls in and who visits your site -- that's the stuff that gives you value: the community you've helped cultivate.

Best of luck to you, I know you'll do great things!