Booting 5 OSes? Is this possible?

[Zachary Uram <netrek@gmail.com>]

I wish to setup on the same hard disk (500GB):

Ubuntu 9.04 (64 bit)
Debian 5.01 (64 bit)
MS Windows Vista Home Premium (64 bit)
MS Windows 98 (32 bit)
MS Windows XP (32 bit)

I want to allocate 50GB for each.

1) Is this possible?
2) How do I setup grub (or lilo) to do this?
3) What order do I install each?
4) How should I handle setting up the partitions?
5) Any special tips?

Zach