Regarding backups, I was just playing with Acronis Home version and it looks pretty good, a lot of options (includind sector by sector image, scheduled backups and more) and is pretty fast.
Acronis works great and will do incremental backups after the first full one is in place.
The enclosure/data cable idea works good too - just make sure you have one that supports laptop size hard drives.
Another good program for booting windows from a dvd can be found here (note that you will need a windows install disc handy in order to create this solution) ---> Bart's Preinstalled Environment (BartPE) bootable live windows CD/DVD