Short bio: Computer Scientist, FOSS supporter (read more)
Tux Machines (TM)-specific
The first time I installed Gentoo, back in late 2004, I used an at-the-time brand-new Dell Inspiron (5150 if I recall) notebook as the victim. At that time, Gentoo was a new world to me, and a confusing one. It took me about a half-week's worth of actual work to get it installed, but it happened, and it was one of the most satisfying experiences I've ever had with a PC.
There was a problem, though. As Gentoo is hugely a do-it-yourself Linux distribution, there are many things that are just not done for you without your explicit consent. Things have become a little easier over the years, especially with the very informative guides and major improvements made to Gentoo's own software, but even today it's still an amazing challenge to get it installed onto a PC and configured correctly (the latter being the more difficult part).
At that time in 2004, the biggest issue I had was getting the wireless NIC to function, and though I did manage it after a couple of days, the solution I had been using was clunky and I was essentially limited to a single SSID to connect to. Despite Gentoo being my preferred distro and one I've been using full-time for 5 years (as of this week), the fact that I had such difficulty getting the wireless to work in the earlier days prevented me from ever using it on the notebook much after that first install. Since then, I've just used whatever distro I felt like testing out, such as Ubuntu or openSUSE.
Well, a couple of weeks ago I upgraded the hard drive in my notebook since the previous one in there was dying, and for some reason I got hit with the idea to install Gentoo again and see how things have improved -