I have been a Mandrake user for about 2 years now. I think they have a fantastic product that is easy to install and basically gives me everything I need to get my work done in an efficient manner. It's install is as easy as MS, and it can be as easy to use as you want.
I had an extra HD and an old Debian CD hanging around so I decided to give it a shot. Using the old CD was a mistake. I couldn't get it to work with my local network or get dhcp working. It was an old distro (2.1). After hashing with it for a few hours I scrapped it in frustration.
Somewhere in trying to get my net card to work I came across this install tutorial [zorka.com]. It outlines the process of how to do a internet install. Basically you copy 6 images onto floppies which puts enough on your computer to reach out into the internet and grab the rest. To my amazement the process worked. I opted for the simpler program selection process. After grabbing all the programs and libraries off of the net it was pretty smooth. XFree86 took a bit of meddling to get working, but it wasn't too bad.
For those of you who know nothing about Debian, it is basically split into three levels of of stability. Stable (Potato)is frozen and solid (and really old), testing (Woody) the place most of us would want to be, this is about the level of most commercial distro, and unstable, bleeding edge.
What the floppy/net install left me with was a nice safe and boring Stable (Potato) version of Debian. I couldn't stay there very long. I use this go-woody script [qref.sourceforge.net] to update to Woody and did a ' apt-get update && apt-get dist-upgrade'. That went well for the most part.
But.. It wasn't perfect. I had to mess with X for a a very long time. I ended up hand editing the XF86Config files with vim to get it launchable again. The configure utilities just wouldn't work properly for me. On thing that got me was that I couldn't get X to boot into the right server. It kept booting into SVGA. I edited the XFServer file but it made no difference. In my opinion X is hell without an accelerated server, so I was going to scrap it. Then I did a ls -l in the X11 directory and noticed that X was symbolically linked to the wrong X server. So, I relinked it to the Mach64 server and all was good. That took me at least four hours to figure out.
The phrase that fits best for me in retrospect is "assembly required".
Okay, on to the good stuff:
Apt is amazing. What ever I want I can get and it is just a command away. This is way better than the rpm system. Once Debian is installed it is always as current as you want it. You never have to buy/burn a new CD again.
Want to have the latest and greatest just:
apt-get update && apt-get upgrade
Removing stuff is just as easy.
Debian would take over the world if it just had an easier install.