I've done some research and asked a few experts, but I thought I'd also get the opinion of some active option traders on here given there's probably at least a few with a lot of experience. 1) With regards to wash sale rules and tax accounting, am I right in assuming that as long as you close all your trades out before December 31st and realize all gains and losses, and as long as you don't re-open "materially similar" trades within 31 days, wash sales shouldn't be an issue? 2) As far as what is a materially similar trade, what about the following: a) An Iron Condor in the SPX, followed by an Iron Condor on the RUT. These should be different enough right? b) A 200 strike straddle on the SPY ending in December, and a 200 strike straddle on the SPY for the January cycle. Basically, are all option contracts that are DIFFERENT month expiry's considered "materially different" trades? 3) XIV vs ZIV. One tracks 1st and 2nd month VIX futures, and one tracks 4th to 7th month. This is a tough one. Do you think they are too "materially similar?" Hopefully I can just trade during the year without worrying about wash sales, and close everything at the end of December to lock in all gains and losses. Then for 31 days starting in January, just trade different enough securities that they don't count as a wash sale. Then February to December, do whatever and rinse / repeat. Does this sound about right, or am I missing something important for active trading and wash sale rules? Thanks a bunch for the help