I'm nowhere near a ruby developer, so i don't understand how most of the things works, but had cero trouble installing gitlab. Even when it throws some strange (for me) errors on some gems, it was just a matter of googling to solve the problem.
Some years back i was able to tolerate when a webapp needed serious fiddling in a) apache configs, b) php configs and c) manual mysql database setup.
Nowaday i expect something to run and have as few steps to install as possible. It wasn't even so much the many steps in between but the stuff that just didn't work as given in the installation guide. Turned out that some answers were in the gitlab Troubleshooting Guide. And then some stuff just didn't work, because at that point resque was removed (if i remember correctly, i don't even know what resque is and i don't really care, tbh). Now, after this took me 2 hours to get it running, half a day was spent with a) log in, b) find something not working, c) google, d) log into server and fix, e) repeat.
I'm no ruby guy, too, but i would've thought this goes much smoother nowadays.
I was using Gitlab for 1 or 2 weeks back then, but when the password reset didn't work it really made me think if i want to go through all that again on the next major update. So i turned to gitblit (which i rejected before because it can't do pull requests).
Edit: Don't get me wrong, i liked the Gitlab interface, it's very polished and nice, and what was working was working fine. Still i wouldn't want to maintain it. Maybe it's all better now with 5.0 :)
I'm sorry to hear you had trouble installing GitLab before. Installation should be a lot better now. We replaced resque with sidekick. Also there are pre installed images available from http://bitnami.com/stack/gitlab
Ah, sounds great. I think you should really advertise those packages more! To be honest the 5.0 installation guide still looks terribly long. No way i would go through that again. BUT now there are packages.. hopefully for 5.0 soon.