The file format isn't what determines how hard getting good tags and album art will be (except maybe WAV, which has limited tagging ability). If your current music is well tagged, I would think any good program for translating that between, say WMA Lossless and FLAC (or ALAC) would preserve the tags. In my experience, EAC doesn't pick up album art, so yes, that's a manual step for me. My understanding is dbpoweramp does do album art well, and I believe it has access to more database information for getting the information to populate tags. I don't know about the options on Mac, but doubt if WMP is a viable Mac option. I prefer FLAC to ALAC as (1) I don't have Mac, (2) I don't use iTunes, (3) it is proprietary format which isn't natively supported on my Squeezebox players (supposed to be on Radio, but I don't believe the native ALAC decoder is actually completely operational - plus there's my Boom and SB3). Most of the tagging headache is usually with the initial ripping of your CD collection, and if those tags are in good shape, it's a lot easier to stay on top of tagging as you incrementally add to your collection.
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