I'll need to Bootcamp probably due to not wanting to lose those Microsoft only games, outside of the rebooting, is it a pain?
It's really only a few extra steps to installing Windows on a fresh computer. You run the Bootcamp assistant in Mac OS which will walk you through partitioning your hard drive to allocate space for Windows, load up the Windows installation disk, reboot and then Windows installs.
After Windows installs, you load up the Snow Leopard install disc and run the Bootcamp Assistant setup from within Windows to install the necessary drivers and software. After that, run the Bootcamp Assistant software in Windows and go to the tab to select your default bootup OS, Mac or Windows.
From then on you only need to hold down the Alt button, during bootup after the grey screen shows and the gong-like sound plays, to pick which OS you want to boot, other than the default OS you chose. You can also go to ATI's website (assuming you get a 2011 Mac) and get updated drivers for your GPU, since the Snow Leopard ones may be outdated.
The only pain I know if you're trying to install Windows itself and you get the error message saying there isn't enough continuous free space, because you've been using the Mac OS a while and files are all over your hard drive. The message is telling you to defrag your hard drive, but Mac OS doesn't have a manual defrag tool, because the file system doesn't benefit from it. You'd have to get a third-party app, if that were the case.
either Mac or replacing on my own but no idea if the software restore would be tough
As for software restore, is if you're using Time Machine now for your backups, just load up the Snow Leopard installation disc on your new Mac, reboot, and do a Migration not Restore. Plug in your external hard drive with the Time Machine backup and choose that as the source for Migrating. Depending on how much data there is, in a few hours or longer, you'll have all your apps, documents, mail, etc loaded up on your new machine with your same username and whatnot.