Some Media Management tips:
1) limit your session to just the files you actually have (that is, make sure nothing is missing)
2) Render-in-Place all H.264, JPG, TIFF, and PNG graphics clips to ProRes so now the clips have embedded timecode and (preferably) unique file names
3) for camera clips with embedded audio, my opinion is you're better off if you strip the sound out as a WAV file that lives in the session
4) be aware that Titles can be a bit dodgy and don't always survive the changeover with Media Management. (I would say the same thing with Fusion sequences, which I would render out and treat as a separate transcoded element).
The simpler you make your session, the better the potential for Media Management. The moment you have a filename clash or a timecode problem, it can fail. If your file copying is failing for another reason, try Nikolai Waldman's Resolve Collect and I bet it'll get you at least 98% there without errors. His program has been a lifesaver for me over the last 6-7 years.
http://www.niwa.nu/resolve-collect/Another possibility (which I haven't tried) is EDLSpy for Windows:
http://edlspy.felixhuesken.de/