I'm sorta in the same boat as you. Have been slowly re-ripping my 2K+ CD collection to FLAC and AAC. The FLAC to run off the home server for my Duet and other devices, as well as archiving the discs, and the other to play on the various iPods in the family. Hasn't been easy and I don't think I can offer much advice other than its been a slow process, but not a problem having two libraries for which the devices can read from. Since I keep them in two distinct places, home file server and Mac Pro, seems to work fine. I use Max to rip in both formats simultaneously and dump the files into the respective library folders.
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