-Tiny Launcher display an error message when the file in the game directory isn't what was expected.
-Tiny Launcher display an error message when there's more than 1 "Jump" file in /S.
2GB is the FFS (Fast File System) Limitation.
If you want to use a larger partition you'll need to use for example SFS.
SFS is also a lot faster on file access.
As for your girlfriend, there's nothing I can do ^^
Actually the database is limited to 500 games, I will extend it to the next update (as you seems to be an hardcore gamer^^)