I find that for me it depends on the item and the person. There are a collection of Moe Berg cards online that came from his personal collection and were slabbed as such and I think I'd pay a (small premium) if I ever chose to go after those cards. On the other hand, cards from someone like Dmitri Young's collection don't do anything for me.
When it comes to other items, as mentioned there's a provenance component. I loved following the Stan Musial auction a little while back and thought the team-signed baseballs were much cooler for having been in his collection (I picked up a couple of WWII team signed balls...)
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