2 bootable systems on a single drive is fine, this is how most hybrid installs are. Once you go above that, however, things tend to get really messy as not only do a whole bunch of limitations jump into the mix (and bonehead assumptions *glares in the direction of Redmond*) but you also need to format and partition the drive manually.
Given that the GPT partitioning scheme needs an MBR wrapper to be backwards compatible to boot systems using the Legacy BIOS (simple answer: everything but Mac OS X) and GPT does not support extended partitions, you can only have a maximum of 4 primary partitions (aka: boot-capable partitions). Apple reserves one of these for its internal EFI partition so you are down to 3. Using one for a Mac OS X partition leaves you 2 left over. You can install Windows on one of these with no problems as it gets marked as "drive 0" in the MBR used by the legacy BIOS and all is happy. Once you install Windows to the last free partition, however, all hell will break loose. Windows expects that it will ALWAYS be installed on drive 0, if it isn't it won't boot. This means you'll need to install and configure a third party bootloader (GRUB, LILO, etc.) in order to reorganize how Windows sees the partitioning scheme and chainload the Windows bootloader.
If you have a drive that is formatted using the MBR scheme and is NOT used to boot Mac OS X you will have a lot more flexibility (the 4 primary partition limit goes away) and you can just follow one of the myriad of multi-boot tutorials around the web. Booting multiple copies of Windows is a PITA no matter which way you go.
Using a virtualization solution such as VMWare or Parallels makes everything I've previously said moot as you can have as many drive images as you'd like; I have 3 or 4 various Windows editions installed along with DOS, CentOS, Ubuntu (x32 and x64) and Moblin.
(note: I haven't done a setup like this in a while, someone let me know if I have some bad info here)
EDIT: What's the point of having a dedicated hard drive for another OS?
More space, easier booting, more isolation, because I can, etc. There are plenty of reasons, just pick the one that you like the best.