Question1. I recently sold a business which was basically made up of just a taxi medallion. So, you could say I sold a taxi medallion that was under a corporation. I owned it for over 10 years. How will I be taxed on the gain I made on that sale?

Answer: A taxi medallion is considered an intangible under section 197. The gain on the sale of the medallion would be treated as capital gain. It would be reported as Section 1231 gain and the tax treatment of the same will be long-term capital gain. If your corporation is an S Corporation, the gain will flow down to your personal tax return and you will pay the taxes on that at your personal tax return level.