I've had my server running on gentoo since 2003 and never once had to put a CD/DVD in my drive to upgrade. Heck, I even started out initially on x86 and then went to ~x86 for some time and then back x86( lots of cruft to clean up but I managed ).
You just need to keep up with instructions given during emerge runs, running revdep-rebuild and perl cleaner also when instructed.

I just ripped Nemo quite a few times recently (Just beginning to rip movies for my media center server) with no problems so far other than I tried picking the longest title once with HandBrake but that title wound up being the movie with commentary. hehehehe.

Now I have started to use -dumpfile option with mplayer to stream the DVD to an mpg and do a quick check to make sure the correct language is expected which allows me to rip three DVD's in a row and just loop them through HandBrake to create the mp4 files. I think it is faster and also saves some wear and tear on the DVD drive.

If you are a contractor for the government.. be a slack-ass like 70% of them do already and bust your ass after work and weekends fixin' up the shack. If you are married with real little ones it's very tough to do, I've been remodeling my house for the past few years and boy has it been quite tough at times. You are a geek, right? Get your nerdy friends off the online games and put them to work.