Use a standalone database file.
After my installation stopped working (wouldn't even launch), I had to reinstall outplayed. Obviously I couldn't make a backup file in this circumstance, and although all my recordings exist in the media folder in the naming and foldered convention that outplayed created them in, the new installation does not recognize them. After working with support I learned the reason for this is that the Metadata for the recordings was lost with the previous installation.
The database for this metadata should be stored in a seperate file outplayed expects to read upon launch, so that future instances of reinstalling or, transferring to an entirely new PC does not result in them being lost, you simply need to copy over the file containing the metadata to the new installation folder and outplayed will know to look for the matching recordings and folders containing them in the assigned media folder.