Ruby would be better than Lisp in terms of being "mainstream" (whatever that really means, but one realistic concern is how easy it would be to find answers to your questions on Lisp programming if you were to go with that.) In any case, I found Ruby very easy to pick up. In the same amount of time that I had spent first learning Python (or other languages for that matter), I was soon writing better code much more efficiently than I ever had before. That's just one person's opinion, though; take it with a grain of salt, I guess. I know much more about Ruby at this point than I do Python or Lisp, but you should know that I was a Python person for quite a while before I switched.
Lisp is definitely quite cool and worth looking into; as you said, the size of community, etc. can change quite quickly. That being said, the size itself isn't as important as the quality of the community. For example, the #ruby-lang
channel is still filled with some incredibly smart people. Lisp seems to attract some really smart people too. I can't speak much about the Python community as I don't have a lot of firsthand experience, but it seems to be "too big" sometimes. (I remember people being quite rude on their IRC channel, and from what I've heard from friends that are really into Python, that seems to be the rule rather than the exception.)
Anyway, some resources that you might find useful are:
1) The Pragmatic Programmers Ruby Metaprogramming series (http://www.pragprog.com/screencasts/v-dtrubyom/the-ruby-object-model-and-metaprogramming) -- not free, but the later episodes are quite intriguing. (The code is free, if you want to download it and see what you'd be learning about.)
2) On Lisp by Paul Graham (http://www.paulgraham.com/onlisp.html). It's a little old, but it's a classic (and downloadable for free).