In all honesty, I would forget about Rails unless you have a really, _really_ compelling reason to pursue it. Rails is such a big framework, you could easily spend as much time learning it (Rails) as you would learning Ruby itself. I would recommend starting with Sinatra and Padrino for Ruby based web frameworks, you'll likely find you never need anything more unless you get a job at a Rails shop.

In terms of Ruby itself, having picked it up myself only fairly recently I would recommend the following:

- unless you plan on maintaining someone elses code, jump straight into Ruby 1.9.

- hang out in the IRC channels, #ruby-lang and #sinatra on Freenode. The community is awesome and really helpful.

- the Sinatra video from Peepcode is really good

- for books, I would recommend "Cloning Internet Applications with Ruby" (ISBN 978-1849511063), "Beginning Ruby from Novice to Professional, 2nd Ed" (ISBN 978-1430223634) and of course the current version of the Pickaxe book (google it :)

- check out thechangelog.com regularly if you don't already

That's about it, good luck with it - I've found it fun so far and am currently developing my first web app on top of Sinatra which i hope to launch in a month or so!