Well, my first language wasn't Ruby, but IMHO it should be as easy as any other to learn. It might be harder once you get beyond the beginner stuff, but that's true for anything. AFAIK there are lots of affordable hosts that have it. But before you buy a host, you should try it on your computer first. Try using the one-click installer and then you can open a browser and go to "localhost" to see the results. If you don't mind working from the command line prompt that will be a big plus.