Figuring that someone getting paid to answer my question would provide a little more of a guaranteed response, but after looking into the service, it looks like the only ones getting paid are the fat-cats who set up the site. According to their site help:

As an Expert you can browse our site ad-free, create your own knowledgebase of useful solutions to use throughout your career, build lasting relationships and exchange knowledge with other worldwide technology Experts.

So much for a dedicated member of the community helping me for money, all they get out of the deal is street-cred which is no different from stack-overflow’s excelent (and free) rating system. The answers turned out to be run of the mill, not bad but certainly not better than other suggestions I had previously received. I ended up figuring out my own obscure answer, and I left learning nothing new about my arch nemesis of systems administration RubyGems.

A rant on RubyGems:

I really dislike rubygems setup, and i’ve had friends give up trying to learn rails after spending a week trying to install ruby/rails/gems/etc. It would be nice if there was a web-cast for purchase, or really really good site explaining how rubygems works and gets integrated into other applications. There are lots of posts on how to get started, but very few people ever talk about it after they tell you to:

sudo make install

If you know anywhere that gives a good healthy overview of how exactly rubygems leverages Ruby and the OS (Unix and OS X )  then please feel free to drop a link in the comments. (And yes i’ve RTFM)