+1 on Octopress (if you like the quick route), else just take some minutes and wrap up yourself with some RoR Screencasts (Railscasts for example) and do it yourself (take a look at https://www.ruby-toolbox.com/categories/syntax_highlighting for syntax highlighting stuff) - it's fun!
I think a fallback solution is never wrong but to be honest, the comfort of a management-free provider is nice to have too. As Google Apps for Business user, i have all i need now.
Even for my private needs, GMail is enough for me. And as JT123 says, it's unlikely that they jump off that ship in the foreseeable future.
If he talks about "considering it" it doesn't sound like an clear YES.
But to put this aside - this risk is up to you - i believe the experience to get out of something stagnant and even move to a new place is worth the experience alone. Speaking for myself, i take every worthy experience i can get to push my horizon further and further.
I can only assume, if you do a good job and gain the necessary skills that you currently lack of, there is no reason he shouldn't consider you.