Should I sell my Tokens and realize a loss before year end?
Disclaimer I have now been asked almost a dozen times about the "Wash Sale Rules" and whether token holders should sell and repurchase tokens before year end. The Wash Sale rules (IRC Section 1091) provide that if you sell a security at a loss and repurchase a substantially identical security within 30 days, your loss will be disallowed (and added to your tax basis in the purchased security). People have been hearing that the Wash Sale rule doesn't apply to tokens because the IRS has not designated tokens as securities. (Remember that the characterization of tokens as securities by the SEC or as something else by the CFTC is not relevant for tax law purposes. Tokens may be securities for some purposes and not for others.) If that's true, you could sell your BTC today and buy back BTC an hour later and trigger a loss that you can use to offset capital gain (or up to $3,000 of ordinary income) from some other source. That's a very reasonable argument...