I just want to pipe up here and validate that you're right to feel this way. I also want to thank you: I've been bothered by the often caustic tone of this forum for a while, but I think witnessing this thread has finally pushed me over the edge to close my account. As a bootstrapper I've probably enjoyed more success than most of the other participants here, but all I can think when I read some of the comments that come in early on threads is that if I had gotten the same type of feedback several years ago, I would have been more demoralized than encouraged.
To your topic: I've been through the exact same transition that you're eyeing yourself, including the Ruby and rails background. I can't claim to have many answers other than what worked for me, but feel free to hit me up privately. I'm pretty easy to find online.