My Linux machine has vented its holy smoke and I am currently stuck with Windows, so I am talking from memory:

Uploads: I kept a list of uploaded files (a slightly massaged output of recursive ls emptool command) and created emptool command scripts (by a Perl program) that 'automanually' created each necessary playlist and uploaded songs individually. It took quite some time to evolve this from album-by-album to more automatic version. (And I am affraid I lost them now... )

Tags: grip I used for ripping and encoding used a V1-only tagger, though I believe the current version is V2 capable. I think I used a demo tagging utility that comes with id3lib to do ID3V2 tagging (from a Perl script) and it worked OK. Alternately (IIRC), one can use a series of emptool set directives (from the upload script) that identify songs by the beginning of the title (once in the correct playlist, of course), but then you have problems with different versions of same song etc. Much better to prepare ID3V2 tags correctly.

MP3TagStudio Tony is swearing on is very good and lends itself to a certain degree of automation (not the kind Linux people are used to, though: no scripting support, just set of rather clever tags-from-dir/filename and vice versa modes). If you have VMWare or a Windows machine with Samba mounts, it can be very handy fot V2 tagging if your dirname/filename structure is systematic and informative enough.

Finally, it should be understood that emptool has never been advertised as nothing but a stop-gap measure. Did you give Jemplode (Java semiclone of emplode that uses emptool low-level code - the only thing Mac users have) a try?

Good luck!

Dragi "Bonzi" Raos
Zagreb, Croatia
Q#5196, MkII#80000376, 18GB green