There a sort of Vista type system restore possible without having to make complete images of the OS partition. I’ve only tested this a VM where it works, but usually if things work there they work on real hardware too. The only snag is that you cannot do it with the BOOT partition of the system. You can do it with any secondary OS installed. The next time you reinstall your machine, do it twice with the first OS going into a small partition. You can use a vLited 32 bit version for the first install. Depending on your memory and how much you can vlite out first it should easily fit in a 4-8 GB partition. Remove everything that can be safely removed without completely breaking it (printer drivers, languages, speech etc. use lots of space and can allways be safely removed, but theres much more). Don’t spend time pondering whether you should remove something you might need later on because you won’t be using that install for anything else than installing a boot partition and making/restoring shadow copies of the OS partition you install next. Install that and then install again the way you would normally do. The second OS will be the one you will actually be using. Shadow copies made of the second OS’s partition can be reverted back to if you boot into the first OS first, revert and then boot again normally, into the second OS.
The shadow copies can be made by the second OS while it’s running but this will give you a black screen saying that the OS wasn’t shut down properly when you revert using that shadow copy. Usually that isn’t a problem but it’s cleaner if you boot into the first OS to make the shadow copies (restore points) of the second.
I tested by making a shadow copy of the second OS then booting into it, clobbering the registry big time so it gave a nice blue screen upon reboot, then booting into the first OS to revert. The second OS booted perfectly again after the revert.
It will cost you the 4-8 GB for the boot partition but with nowadays disks that isn’t such an issue and you can have restore points in Server 2008 ! Made in a couple of minutes and reverted to in about the same amount of time. Just my 2 cents …