Regarding Wash Sales. I think I'm ok to sell one option at a loss, and a different one I already owned with a gain. It sounds like the point of the rule is to not sell at a loss, and THEN repurchase the same/similar within 30 days, to fake a loss.
This is what I read at Scwab:
Key Points
The wash-sale rule was designed to prevent investors from selling a security at a loss so they can claim tax benefits, only to turn around and immediately buy the same security again. Even investors who have no intention of breaking this rule can get tripped up by it if they use an automatic investment strategy, such as reinvesting dividends, potentially costing themselves some tax benefits in the process.
- The wash-sale rule was designed to discourage people from selling securities at a loss simply to claim a tax benefit.
- A wash sale occurs when you sell a security at a loss and then purchase that same security or “substantially identical” securities within 30 days (before or after the sale date).
- If you end up being affected by the wash-sale rule, your loss will be disallowed and added to the cost basis of the securities you repurchased.
Does this sound right to anyone (that I'm safe selling my 2021 calls at a profit in the next 30 days after selling my 2020 at a loss today)?
In the end the numbers will be added up between your gains and your losses. It you sell at a profit you will just have less losses to write off.