I'm on the other side of the filename issue.
I don't care a whit about the 'real world' name of a file. It's the metadata describing the file contents that is important.
What would be nice if JR could come up with an 'optimized' auto-name/rename scheme for files. You could even stick with a hashed filename to be able to stick with an 8+3 convention.
Embed the metadata wherever. A filename 'key' could be internal to the actual file as well as being kept in the LS database **and** represented in the actual filename. Think of it as a brute-force auxillary indexing method. This scheme would (in theory anyway) improve database size and performance as well as recoverability from a blown database or NTFS directory structure.
We do this all the time with Oracle and DB2 databases behind some really huge SAP systems. On those beasts it does improve performace, acts as an additional sanity check on dB consistency, and on more than one occasion has been a life saver recovering from some serious system (ok, people) errors. Gotta love those junior DBAs........
When syncing to an external device/player, a 'sensible' filename could be restored/reconstructed from the metadata. This is necessary because most/all players use the filename as a part of the user interface & presentation. Downside, it adds an extra internal step to sync activities. Upside, it auto-builds consistent filenames on a player. It's not too far fetched to allow the setting of a few filters so that the auto-build of the new filenames could follow a user-defined pattern.
To keep everyone happy, the use of a scheme like this it would be an optional setting.