Hi John,
Just to throw some ideas out on your first alternative, if you wanted to stick with Win95 on the 2nd system, NI does still provide the peripheral drivers on the website
here.
Basically all you need to do is copy the contents of the Windows 95 installation CD and all of the peripheral drivers to a temporary folder on the hard drive (make sure they are unzipped first as Win95 doesn't have a built in zip utility like Win2K/XP). Then boot to DOS and run the Win95 installer directly from the hard drive.
As far as getting the files onto the hard drive, if you already have some other OS installed on the controller, great, copy them across the network or use a USB-CD drive. If not, you can copy across the network by booting into DOS with network support. There are details in this KnowledgeBase document here:
DOS Ethernet Drivers for the PXI-815xB and PXI-815x, VXI-850, VXI-860 and VXI-7xx Series Controllers....
So ultimately I think you will be successful choosing either to go with Win95 or Win2000 on this issue. Best of luck!
Joshua Hernstrom
PXI Software
National Instruments