After reinstalling so often with hardware changes, and just window house keeping I have a process in place that stores and backups all critical files to external storage devices or NAS.

I have my robform password file (encrypted) and favorites on dropbox so I never have to worry about losing it. Outlooks PST, images, videos are all stored on a 5TB server in the other room and backed up to a NAS.

When I do have to reinstall a new OS it takes me very little time to get back up and running. So for me it is a simple thing to do just restore to a ghost image of my OS but I know for most folks it can become a monumental task. So I understand your hesitation.