Installed Debian 3.0r4 on a spare machine, mostly out of curiousity. There are a enough folks fond of Debian thought it might be worth another try.
First, I made a horrible mistake. Downloaded, burned and installed from 9 ISO images (7 installation, 2 updates). Trying to be a good bandwidth-citizen by downloading via bittorrent, and leaving the client up long enough to contribute back as much as I had pulled down. After burning the CDs it (belatedly) occurred to me that with 9 CDs I might be in for a lot of disk swapping. Turns out, that is exactly what happened.
To be fair, I do believe the Debian installer is much improved over the last version I tried. Still - getting two disks partitioned and formatted as ext3 took an awful lot of trial and error. In addition for some reason the video driver used during the installation painted characters on the screen about as fast as a 9600 baud terminal.
The installation (or perhaps more accurately the packages in the installation) ask a lot of questions at random times during the installation.
Ideally you would like to answer an initial set of questions up front, then go do something else while all the download/unpack/whatever batch operations run. At the end you could do configuration on all the newly installed software. This is not what you get with Debian. Add random install-stopping questions to a lot of CD-swapping and the whole procedure was rather tedious.
In the end Debian booted to a character-mode 80x25 login (giant letters on a 21” panel) – and at this point I had lost interest.