To make deployment easy and smooth, it was decided to use network booting and running Windows from a RAM disk.
The machines had 8MB of memory and it was found we needed 4MB for Windows to be happy, so we had a 4MB RAM disk to squeeze everything into. A colleague spent a lot of time slimming Windows down, but got stuck on the printer drivers. They had 4-5 different HP printers which required different drivers, and including all of them took way too much space.
He came to me and asked if I had some solution, and after some back and forth we found that we could reliably detect which printer was connected by scanning for various strings in the BIOS memory area. While not hired as a programmer, I had several years experience by then, so I whipped up a tiny executable which scanned the BIOS for a given string. He then used that in the autoexec.bat file to selectively copy the correct printer driver.
Project rolled out to thousands of users across several hundred locations (one server per location) without a hitch, and worked quite well from what I recall.