New
#51
I might be too late to contribute to this thread, but I have a dual-boot machine and I have no problem with sharing data files between the OSes. Moreover, I have never bothered with moving C:\Users\... files, syncing, sharing and so on. Heck, I even have search completely disabled on my machine since I have no need for it whatsoever.
The simple answer about using same data files between the two operating systems is to put those files onto a separate drive. In a dual boot scenario I'm thinking three separate drive (physical drives, not partitions). One for one OS, one for another, and the third one for data. I would keep all Windows-created folders where they are. Who said that my stuff has to be in C:\Users\username\Documents? I never put anything there. If y files are in H:\files\ then this can be accessed from any OS. You probably want to set security settings such that the said folders can be accessed by "everyone". On a single-user machine that's not a problem.
This completely solves the problem of accessing data. If you want to run the same program in both OSes, then clearly you would have to either set them up separately, or point the program to store configuration files, etc. on the separate data drive rather than in the default location. There are some programs that won't allow that, but I personally either don't use such programs, or use them on a single OS, or if absolutely necessary, just set them up twice.