I would recommend you skip rails and go for Sinatra. I found that rails had too much for me to learn to find it useful, a bit overwhelmed by the convention V's configuration thing. That is the rails convention didn't really match my own.

Sinatra doesn't have all that. A combination of Heroku, Sinatra, and DataMapper (nice, cleaner, simpler alternative to active record) and what you have is a very easy to deploy application.

I'm doing the above, and doing it on Windows (sorry, I'd love to use Linux but my wife uses this machine when I'm not and has some apps that are not replaceable, and I don't want to mess around with dual booting. So when I get FU money I'll be Linux all the way).

If you have any questions I'd be glad to help.