This is hardly a complete answer, but it may help. I have a development machine here with Windows 7 and Kubuntu; I used a 128 GB SSD for Windows (the whole thing) and have Kubuntu dominant on my other three hard drives, with a limited partition made for media files in Windows. Any time I do have to reinstall Windows, I simply pull out the SATA cables from the back of my other hard drives first. After the install, I power down, plug them back in, power up, and set up Windows to use the proper directories (on the other hard drives) for user documents. I've done this more than once and it's yet to give me any trouble. GRUB even recognized it after a quick device scan.
I understand that you're trying to do this on a single hard drive, but everyone else has already highlighted the issues behind this (mostly with Windows being a complete #$%@&* about having to share). If you can get a cheap SSD or even HDD, and plug it in in parallel, then keep your more-responsible OSes on the major drives, it should make the process simple. You won't even have to worry about partitioning.
(I will also say that if you do do it this way, you'll save yourself a lot of trouble by keeping every drive either MBR or GPT; try not to mix and match. It makes booting more complicated than anyone wants to deal with.)
Best of luck!