I have a couple of rules for when I make big purchases myself. Maybe this will help you.
I'll only spend what I consider to be a lot of money if I feel as though the card I'm buying is easily resold at a later date should I need the money back. That rules out most esoteric cards but it also means I generally see a pretty good return on what I buy (largely spending big on Cobbs and Ruths, for example. Easily sold later and usually for more than I paid).
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