TLDR: Do sales of long puts at a loss and purchase of underlying stock within 30 days qualify as wash sale rule?
Let's say I am a long term investor on SPY, and I buy $1,000 of SPY every month on the first trading day of the month.
To protect my position from market crashes, I also buy at-the-money SPY puts with an expiry date of 1 month and sell it a day to expiry a month later.
For all 12 months in the last year, the SPY kept making higher highs so that in the year all my 12 options expired worthless.
Will I be able to claim all the losses of my SPY put positions on my tax return, or will the wash sale rule apply in this case so that the SPY put losses are used to offset the cost basis of the $1,000 SPY shares that I buy each month?
What if an alternative ETF is used?
What if I were to buy protective puts using an alternative underlying ETF that still tracks the S&P 500 (IVV, VOO, etc). Would selling IVV put options at a loss and immediately buying SPY stock qualify as a wash sale?