Anyone have any good Tax Harvesting tips for options? I read one idea for coverting your long-term losses on a stock position to short-term losses. 1. Sell your long-stock 2. Buy a deep ITM call option (triggers the wash sale rule) 3. When the call is exercised a new holding period is created 4. When this stock is sold the loss is realized as short-term
It probably doesn't work, but I suggest to ask for free advice from professionals on fairmark.com's message board. If you substitute your stock position with a substantially equivalent options positions, you shouldn't be able to convert the holding period to your advantage.