I use all of em,, XP, W7 and W 8.1 and all I can say is XP is sloooowwww There is no reason unless you like sitting around for 3 minutes just to start a computer to stay with old OS systems.
And Sonar doesn't care which system you are on. old files open on all new versions without a hitch for me. Only the odd 3rd party vst glitch.
Don't use bundles, use CWP and per project folder.
Your tech recomondation to keep yur old drive is a good one, that's how I upgrade, I leave my old hard drive alone and install a new one. The old drive becomes a data drive and that way there is no danger of losing old files.