The easiest install will prolly be Dos.
You might be able to getaway with Win98/Me.
Steps:
1) FDISK The Drive, create 2 partitions. 2nd Partition enough to hold the installation Disks/CD.
2) Format the 2nd partition with /S option (Copy the system files)
3) Copy the installation disks/cd into a folder.

Now u may need a Boot Manager to be able to select which partition to boot from after the OS is installed on the 1st Partition.

There is some free partition managers out there, but ya may just want to get a copy of ultimate boot cd, and add it to the 2nd partition. this may require editing. but it comes with some nice tools.

Good luck with this