I've been a Gentoo user for a very long time. But recently, I bought a laptop and rather than wrestle with Gentoo again, I decided to try the much-praised Linux Mint. It just worked, and it allowed me to build my own code and create a full development environment for all the languages I regularly use (C, Python, Node, Java, Clojure), as well as cross-compiling for android development on Eclipse.
I decided I was tired of the breakage and confusion on my desktop. It was out of date, Gentoo wasn't keeping up, and I wanted something that just worked. I backed up my desktop to the house NAS, which took about a day. I put the Mint 15 DVD into the reader and within an hour it was fully installed, up and running and everything. After I had a working OS, I used apt-get to install two critical pieces of software: screen and openssh.
From my bedroom, I made a list of about 90 things I had to have installed on the desktop. Now that I had ssh and screen, I used the laptop to SSH down to the desktop and open a screen session. In one window, I started a restore of the /home directory; in the other, I sent the list of packages to apt-get. Then I went to bed.
In the morning, my system was (almost) completely ready.
The (almost) problem was that I had two issues. First, I'm old-school; I had to figure out how to disable the oh-so-modern alphabetical sorting on terminals; I want it ASCIIbetical, the way Gnu intended. Second, and more troubling, it was running an older version of Gnome, not the up-to-date version of Maté. I really had liked the Maté I'd seen yesterday. That turned out to be a simple setting. Some software packages are fairly out of date in the "stable" version, but I soon had happy modern versions of Handbrake and Wine installed.
Other than that, it was completely without angst or trouble. It's very pretty, responsive, and working. It runs my Windows VirtualBox nicely (necessary for doing IE8 testing), shows all my movies and plays all my music. I haven't tried out GTKPod, Azureus, or running Windows natively yet. I haven't done any major development with the desktop-- I'm not working at home with my current job-- but so far I'm very happy. This was even more painless than the upgrade from XP to Windows 7.