Kinda interesting how I ended up here. Looking at that Simpleology stuff, ended up on Joyner's forum, read your "I'm crap at marketing" post, and now I'm reading about Ruby on Rails, which I've been using full-time for almost a year now. 🙂 Anything I say about it is going to be very subjective, I'm afraid 😉
Consider that you need to take risks to get the big prize. I started with Rails a year ago when it was a complete unknown. Now? I have work coming out of my ears because I'm one of the most experienced with it and the demand is higher than supply. It's not Java.. demand didn't grow slowly.. it's rocketing! A risk that paid off.