I'm going down a sort of similar road. I've been developing software for
10+ years, but only now have I begun thinking about switching from doing
server-side/mid-tier stuff to more cutting edge web development. I'm a long
way from any sort of expert on anything, but I think my advice will be ok
for a noob.
First, and maybe most obvious would be to learn HTML and CSS.
You can develop Rails on windows, but
I'm not aware of any ISP that runs Rails on Windows.
Developing Rails apps on windoze in no way prevents you from deploying
to something else. I develop my personal Rails apps on a Mac and
deploy to a Gentoo Linux box for example.
If you don't already have it, get the 2nd edition (right now only available
as a PDF) of the Agile Web Development with Rails book from the Pragmatic
Programmers website. It's the single best reference to start with.
Ruby for Rails by David Black is very beginner level also.