Imaging is no solution to move an OS installation from one machine to a different one. Never was, never will be. There is no "clean" way but to reinstall the OS and all drivers/apps on a new machine. I don't know about "injecting" drivers while restoring, but i'm willing to bet that you'll run into a lot of trouble when you try moving the OS that way. A complete reinstall is no big deal if you do it the right way. Just document anything important you install/configure (a small textfile would be sufficient), and recreate all steps on the new hardware. This takes some time and brain work, but it'll make reinstalling very easy and efficient. It's also possible to "move" the config of many apps, by saving certain registry keys and config files, and restoring them on the target machine/OS.
Btw, you don't need any kind of OS image for DOSBox games. DOSBox is a "virtual environment", so it should work on a different computer/OS just by installing it and configuring it correctly (i.e., like it was configured on the "old" machine/OS). It's important to use the same mountings you've used on the "old" machine.
For Windows games, i'm using a workflow that works amazingly well. I'm installing the games on a test machine, and then scan the file system/registry for any changes (there's tools to do this). Most of the time, there's only one or two registry keys added during the installation, and the game files of course. By importing the registry keys on my "main" PC and copying the game files, i was able to get even recent games to work perfectly (online play, updates and all). You'll sometimes need nocd-patches, but these can be obtained easily. Another benefit of this method is that you don't get the crap that comes with modern games, like hidden device drivers. This process worked perfectly for S.T.A.L.K.E.R., C&C3, C&C:RA3, F.E.A.R. (+addons), Quake 3/4, and many more games.