A few years ago, I purchased premium seat licenses for an NFL team directly from the team (i.e., not a resale). One of the benefits of the seat licenses is "One complimentary reserved VIP parking space in a preferred parking lot”; this benefit extends through the entire 50 year life of the license (note: they also sell less expensive seat licenses, which allow holders to purchase stadium parking). Parking is allocated at the start of each season and is in a designated area (e.g., I don't have "parking spot #1234," instead I have parking in Zone 1). This year, I've sold my parking for various games for over $1000 on Stubhub, and thus will be getting a 1099. My two questions are: (1) Can I treat these sales as LTCG under the premise that I acquired parking at the time I purchased the seat licenses? And (2) Can I ascribe a tax basis to the parking? Since the team also sells parking to certain lower tier seat license holders at, say, $100/game, can I use that price as tax basis? The argument is that my seat licenses were priced at a premium to those who did not get complimentary parking. I would argue part of the higher cost of the seat license was the value of the "complimentary parking" space. So I would use the price the stadium sells parking for each year to seat license holders as the tax basis for the parking. Many thanks for your feedback.