Well, TR has decided I can't paste a link to a page I found that has some information on it that I thought might be of some use to you. Try using duckduckgo (it's a search engine) to search for "freebsd ruby library and path locations" (without quotes), following the (probably first) link to a site called "zytrax", and going to the part of the page called "Ruby Library and Path Locations". It might help; I'm not really sure.
I don't remember exactly what I did to get stuff working here. It just works; I haven't touched it in a long time on my local setup, precisely because it just works. I think Apache is just kind of a perverse pain in the arse in general, frankly. I think my next webserver will be using something simpler to maintain -- maybe nginx or something along those lines -- unless I end up having to tackle something where someone else sets the requirements, of course.
I'll let you know if I think of anything else.
Keep Up with TechRepublic