Ask the buyer if he is willing to negotiate or if he wants to know the most you can pay. If he'll negotiate, make sure the first offer is credible. If no negotiations are possible, my advice is to make the absolute best offer you can for the card - hold nothing back - and state it as such "hey, this is the best I can offer for the card.' Mention the family connection to the card and hope for the best. If you actually put the offer up and he turns you down you can rest easy knowing for sure.
While I don't own any really rare or super high vale cards, I imagine those that do appreciate serious offers. Id say at LEAST better than 65% of ask...
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