I just set up a dual-boot on a 4-5-ish year old machine for a family member, who wanted to be able to play some games that wouldn't run using WINE, etc. (I figured that rather than turn the kid off of using Linux because of a game or three, might as well re-use an old Windows ME CD and let her play the games and see how much better Debian is in general at the same time.)
It went flawlessly, without a single hitch. Both operating systems booted afterward without any further modifications necessary. Wrestling with driver crap on the Windows side was much more of a pain (16 colour display? wtf?) than the Debian installation. The hardest and longest part of the Debian installation was probably downloading and burning all the ISOs (I want to have a full set on hand, so I downloaded them all).
All I had to do afterward was install a vanilla 2.6 kernel and ndiswrapper + ndiswrapper kernel modules, download the Windows driver on another machine and transfer, configure the network and done! (The wireless device I was using was a Linksys WUSB11 v3.0.) No compiling, no custom kernel, nothing. I think it's an even better setup on the Linux side than before, which was using some funny hack for the wireless, which wasn't particularly reliable (I didn't do that install). It was also running Ubuntu previously, but the switch off of that mainly has to do with Debian's flexibility and wide range of supported packages (and, um, my involvement with it) rather than any particular dissatisfaction with Ubuntu.
All involved in the making rock my world like crazy.
I feel like hugging people now. Especially after the Windows installation, last night...