We all take losses on things that we like. This is a hobby. Some people spend $5000 on other hobbys with zero chance of recouping that cost. Lets say someone likes to spend money traveling and spends $6000 on a cruise and not the cheaper one for $1000. Thats a $5,000 difference that is gone forever except the pictures you take on the cruise.
Someone may want to pay $5,000 more than someone ever would on a card. The answer just shouldnt always be 'what its worth'. If there was one 1983 topps signed card available of a guy that played for 1 year and it happened to be my brother, i know i would pay thousands more than the 'market' (market being other signed 1983 cards with POP of 1 with same type of player)
Anyway, the only issue i would have if i am going to pay thousands more than the next guy is the chances of seeing another one at auction in the next year or two or whatever time table i am good with. If i am confident another item wont come up for the next 10 years, that would allow me to pay more etc
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