Gotta love the 3rd gen classic
20 GB 3rd gen w/ 64GB CF card, using the green adapter board. Works mostly fine, some issues waking from sleep, likely due do the SanDisk card. Might eventually swap to an iFlash solo board but for now it’s good enough.
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Which software do you use for syncing?
I was using iTunes 12.9.5 thru Retroactive but then the install crapped itself, still not sure what the issue was. Ended up digging out a 2012 Mac Mini and doing a clean install of Mavericks with iTunes 11.3.1. If anyone else is having issues syncing a 3rd gen, try putting it in disk mode then connecting it, fixed the freezing issue when syncing for me.
I switched to manual management of my library and am working my way through it with MusicBrainz Picard, Easytag etc. because the thumbnails were often broken, labeling sucked. Now I am having a hard time making iTunes monitor my curated folders and need to "add to library" every time I finish a folder. Sucks when you have to sometimes go back to a curated folder and change minor mistakes..