Fred flies to LV and buys 200 chips. Keeps 100 and puts the rest on ebay. I dont think the IRS will 'buy' his plane ticket, car and hotel claim. If I go and pick up 8000 chips its another matter. ... CPA David Spragg

David; I know that you are a CPA ... but that does not make you Jim Perlowski!

How about in your ficticious scenario ... if "Fred" drives an hour to Atlantic City and buys 50 chips ... every time a new chip is released.
"Fred" keeps one chip for his collection and puts the other 49 on ebay and claims "it's just a hobby ... I don't need to report that".

Suppose it's not 50 chips that Fred buys, but a couple of dozen chips each time a new LE is issued ... to be put on ebay. Fred's defense to the IRS agent is; ... "they were only duplicates I was trying to sell so that I could purchase more chips for my hobby."