Originally Posted by FenderP
Going FLAC --> WAV --> ALAC will lose tagging since WAV can't have tags.
The software should be able to retain the tags when it transcodes it. Now, if it will work flawlessly when accessing your music in iTunes is another story. I think thats why I would prefer to enter it manually, that way I'm sure its correct. It would be really time consuming though. I think I'm going to re-rip some of my music just so it handles it smoother (its easier for me to re-rip then do the manual switch over from one format to the other). Of course, as a recent thread showed, that can introduce some other issues (such as one software outputting the same music at a different level than the other one does, so even though they're both lossless, they don't end up the same which threw someone off thinking the software wasn't encoding it properly).
The bonus part about doing it manually is that is the best way to do album art, so if you just do a few albums here and there, you'll make steady progress towards getting your whole collection done before you know it. That can also make it nice for re-visiting albums that you don't listen to as much.
The frustration of handling a music collection (especially using different software for various specific parts of it) is what made me go back to CDs a little while back. Now I think I've figured out a way that will work for me for now (and the next couple of years), and then after I get a real job and can afford some more expensive gear I'll make the effort for the extra quality (and in the meantime put my effort toward discovering music worth caring about the extra quality).