I've shared this before...In Oct 2020 we sold a small farm in California (long term capital gains). Had a low basis and was going to get clobbered in taxes in April 2021. I also had short term capital gains (things like options) that generated about $20,000. that year.
So come November/December of 2020 I sold 20 to 30 stocks, bought back options (buy to close). I would use every loss I could find. These were both short term capital losses and long term capital losses. It worked really well tax wise for 2020. The only problem was I ended up selling quality stocks that rose quite a bit in December 2020 (30/31 day rule to buy back). Some I bought back...Others I looked elsewhere for value.
So come November/December of 2020 I sold 20 to 30 stocks, bought back options (buy to close). I would use every loss I could find. These were both short term capital losses and long term capital losses. It worked really well tax wise for 2020. The only problem was I ended up selling quality stocks that rose quite a bit in December 2020 (30/31 day rule to buy back). Some I bought back...Others I looked elsewhere for value.