There are no set rules in this game. If you applied a strict, disciplined approach to what you would pay for quality Ruths and high end Mantle cards in 2017 the satisfaction you would have gotten from not "overpaying" would not have lasted long as you watched prices skyrocket from those levels.
You also have to decide what you want more, a good deal or the item. Prices for rare items are tough to predict because you never know when two buyers will decide they don't want to wait ten years for another shot. Personally I have more regrets over the items I didn't buy because I thought the price was too high than over the ones where I overpaid. Example: every Jim Thorpe I didn't buy.
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