In my humble opinion, the ballyhoo over the state of affairs between the Debian and Ruby communities is unnecessary.
Why? Because while Rubygems has a different perspective on the Filesystem Hierarchy Standard, Debian (and Ubuntu) have managed to find a way to make an incredible amount of Ruby versions (1.8.7, 1.9.1/1.9.2), gems (libtokyocabinet-ruby1.8, etc), frameworks (ruby on rails, sinatra), and applications (Redmine!) work within their policies. Sweet!
Still, its unfortunate that there are gripes and complaints from both sides of the debate. Personally, I believe that the Ruby community will eventually acknowledge that Debian has their policies in place for very good reasons, and start aligning Rubygems with them. And I have to say I was very disappointed that the debate got so heated that a crucial member of the Debian-Ruby team (Lucas Nussbaum) left his post due to the volatility of the situation.
Anyway, I'm writing this post to state that I have had a very positive experience with using Ruby, Rubygems, Rails, Sinatra, etc. on both Debian and Ubuntu. If you've heard extensive complaints about the two (and they do exist), let me state it again:
I have had a very positive experience using Ruby on Debian and Ubuntu.
Sure, there have been bumps along the way, but hey, those bumps gave me an opportunity to learn something.
Debian is my favorite operating system, and Ruby is my favorite programming language. I'm sticking with them.