Tactical error...
I need to change that trade.
I bought IWM puts.... if those become hugely profitable at expiry, I'll have to take a painful tax hit.
Instead, I need to rework the trade by dumping those puts, shorting IWM directly, and purchasing calls to hedge. That way, I can keep the short position open forever without a tax consequence.
Let's say for example the market drops 50% and I want to dump the hedge. Well, I don't want to dump the hedge literally because I would be stuck paying the capital gain. Instead, I should just keep the IWM short position open (at a large gain) and buy an offsetting amount of depressed stocks. Then over time the gain on the IWM short will unwind and I'll have an offsetting gain on the stocks I purchased.
No realized gains that way. Keep the assets for myself.