[Exhibitman]

One of the reasons I operate an actual card/collectibles business with a resale permit and Schedule C filing every year is so I don't have to get into this "collection-investment" quagmire. I sell it through the business at the cost basis I paid for it. No games, no nonsense. I take my hits on profits, and offset it with whatever losses. If a taxing entity wants to challenge my status, bring it. I have an unlimited budget for litigating.

I know the tax jocks outweigh my puny lawyering understanding, but if it was my deal, I'd keep it simple and clean: sell the item for an agreed price and purchase the other one for an agreed price. Put it in writing, and pay whatever taxes are due on the profit. Not worth your ticket to play around. Mechanically, you can do it as a trade with cash boot, but contractually, just make it two sales.

Now, as far as whether I would make the trade, probably not under the scenario laid out. If I care about the registry and I don't want to eat a ton of taxes, it isn't worth it to me. The fact that Nicolo (forgive the 3rd person usage) has trepidations about it to the point of posting it here tells me that he doesn't really want to do the deal anyway. I am the same way. If you want one of my Maltese Falcons, the price is going to be stroke-inducing to make it worth my while, and if I feel bad about it, nope. Life's too short for regretting a card deal.