The DOS machine has been keeping me entertained with some Monkey Island 1&2 and Command&Conquer lately. I have also been able to successfully dual-boot both DOS 6.22 and Windows Me.

It took a little bit of googling, and a large bit of experimentation but I found a way to dual-boot DOS and Me from the same HDD despite Microsoft saying you can’t. Here are the important bits: both OS partitions must be primary partitions (you can’t use FDISK to do this, you need something like Ranish Partition Manager 2.4); you need to replace your MBR with a boot app that can hide whichever primary partition is not in use (I used Suzhe’s Smart Boot Manager because it will automate the partition hiding).

You should be able to figure it out from there; leave a comment if you have any troubles though.