1099K

Hi JHOG,

I could be wrong, but I would think it would depend on his intentions. Is he buying the cards as an investment or is this a business? 

I have clients that have bought real estate properties as investments in the past. They buy properties, make improvements, and sell for a gain. However, in 2022 it became apparent that they were doing this as a job, not an investment and now they are reporting their real estate "flipping" on Schedule C and may elect to file as an S-Corp in future years.  

I would ask some questions that would give you a feel for the client's intentions. Do they have other sources of income? How long is he holding the cards before he sells? Maybe it started as an investment but turns into a job? How does he pay his living expenses? How much time does he spend on this activity? These are all questions I would ask. 

This is more of a tax question and not a software question, but if he is not in the business of selling collectibles (or whatever the cards were) and otherwise doesn't file a schedule C for such a 'business', then I believe it should be a simple capital gain. I think the schedule C is key.