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JoshInteresting topic, I too am amazed when I see these prices, but when it really comes down to it, 80-90%+ of these items being sold at Mastro, REA, etc. are rare investment quality items, and a $5K investment is really a small piece in the big picture of one's portfolio (assuming one has some sort of investment portfolio, whether it be as simple as a bank account to stocks/bonds to real estate, and I highly doubt the majority of the buyer don't have something together).
Two weeks ago I purchased a lot from the Mastro auction that I paid $4,700 including juice. Yesterday, I won a lot from REA that will run me $5,200. While the $10K layout may seem hefty, I think my $10K here will hold up as well if not better than if I had gone and poured in into say, 150 shares of Altria.
Obviously, not everyone has $10K just laying around burning a hole in their pocket, but this is money that I have essentially budgeted from my income specifically for these type purchases. I think there are a lot of other investor/collectors who think along the same lines, and these are the people who are laying out $5-10K.