Keeping libray & content togther on the same drive will, I suspect, prove more robust. If you could arrange to copy your library files to the
parent of the media folder on the "content" drive, then use the Shift/Option-start-iTunes method to open the library from the "content" drive you might get lucky.
When library & content are in the standard arrangement then iTunes can cope with changes in the drive letters or device IDs as all file references are considered relative to the library file.
The order in which your devices are connected or initialise themselves when you start your computer may explain the random nature of your problem.
tt2
N.b. On a Mac the .itl extension is omitted. The xml file may be called iTunes Music Library.xml depending on the location of the library.
Message was edited by: turingtest2