$%1T happens again

There are times I really want to give Microsoft a collective punch in the neck. After a massive update that M$ does seemingly every Tuesday, I lost all my personal files and some apps on Portabrayne's HDD today. What Recuva did find is a mixed bag of some of the files I thought I lost forever, files from others, and some I never saw before. I saved them all to the external as soon as I could, but I couldn't find more recent stuff that I had on there.

I wonder how far back in Quicken I restore from backup.