Ask HN: Windows backup that survives OS reinstall?

Hey HN,

I need to upgrade Windows 7 to 10 on an important box. Given that it's currently very sluggish, I'm thinking the time is ripe for a reinstall. I could do a full backup, install the new OS from scratch, and then reinstall all apps one-by-one and copy back the app settings and data from the backup, but it's tedious and error-prone.

I also need to be able to rollback the machine to its previous state if anything goes wrong.

Can you recommend any tool that could help me out? How would you approach this?