In the continued saga, this week I got Windows 2000 Professional on and then after some hair pulling reformatted the drive. Why, you may ask? Drivers.
The laptop in question was build around the time that Windows 98 was coming out, before Windows 2000 Professional was released, and it was never officially supported under the latter. Despite that, after installing Windows 2000 Pro every minute piece of hardware was correctly identified, I didn't have to install any extra drivers to get it that far. There were, however, three problems remaining: the built-in video card wasn't working correctly (it defaulted to generic VGA) and the two PCMCIA/PC-Card slots refused to work - with my intentions of using a PCMCIA ethernet card, this was going to pose problems.
Long story short, it completely stumped me. Each device was giving a similar error in Device Manager that there were insufficient resources, but none of them gave detailed enough of an answer to pinpoint what was insufficient - IRQs, memory, etc. I suspect it may have been a memory issue, but it was kind of silly of them to write drivers that were hardcoded to memory above the 64mb limit for laptops that were released back when 32mb was a large amount. After several hours of searching for alternative drivers, disabling other devices to see if it was a problem of something else conflicting, it was just going utterly nowhere.
So last night I took my HD platters in my hand and wiped the drive. Then the real fun began, but that's for another time.