I use VMware and VPC to test OS's as well. But for dual booting, I tend to do windows NT/2k and dos. Of course I am only goind this with smaller hard drives as dos can only use 2 gigs. I know there are programs to make tons of different boot partitions with menus and blah blah blah. I've tried some, but I couldn't find a serial so they expired and I was stuck with nothing...
Theres a updated FDISK program that MS made for Win98 that will let you make a partition higher then 64GB. If I can remember right the readme said it can let you make a partition up to 300GB.
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Really and truely you don't need to get any updates for NT4 if you plan to use SP6a.
and i couldnt find my copy of ie55 so i just went and got 6
You can just patch MS-DOS 7.X to run with Windows 3.1X and then have FAT32 up to several TB's
I just used my HD's CD and partitioned mine