buy the artists you like.....not the ones i do.
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Most of my favorite box sets are in jazz. Just a handful you might consider:
Ella Fitzgerald - The Complete Songbooks
Billie Holiday - Verve and Columbia box sets
Louis Armstrong - Portrait of the Artist
Thelonious Monk - Complete Riverside
Art Pepper - Complete Galaxy Recordings
John Coltrane - Classic Quartet Impulse Recordings
Bill Evans- Complete Riverside
Duke Ellington - The RCA Centennial Box (24 CD monster)
You can't go wrong with the boxes from the Mosaic label, if you like jazz. If you don't, none of these recommendations will be of much use to you.
Depends upon your taste in music and how detailed you want to get.
I've had some box sets and then gotten rid of them because I ended up buying all of the individual releases. The only one that I haven't been tempted to replace is also the most expensive and that is Pink Floyd's Shine On Box set. Since everything in it is "remastered" I had no desire to pursue newer copies as they were released.