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I would say the best time to make an image of the OS partition is just after a sucessful, clean install of the OS AND your favourite programs.
That means when you restore the image (either due to problems or just for an 1-2yr clean out) you will be restoring the OS and programs at peak efficiency and without accumulated bloat and debris.
So if you're going down the image route, I would suggest you back up your important data and then format and partition, for optimum use. Then make your images of the partitions you want.
This means will be able to restore optimal images of your OS and programs partitions any time you want. This way, you won't even have reinstall your programs.
It takes a bit more work at this stage, but will save you a lot of time in the future.
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