From a unique situation due to my primary work being a landlord and an S-Corp business owner I have a tremendous amount of paper losses and the ability to drop down my AGI through aggressive elective retirement funding. In short, this creates an opportunity for me to bury long term capital gains in the 0% tax bracket. For example, in 2018 tax year I completely buried a 100k long term capital gain in that 0% bracket. For the tail end of 2018 I went long more aggressive growth stocks. When SP was at around 2875 and kept this up until April 2019 when the SP had returned to 2875. At that point, my portfolio was up 50% (400k) and I decided I more want to balance my overall risk by moving to what I saw as more defensive equities that paid dividends and also do a bit of an SPX market short. The thinking was the bulk of my personal wealth is tied to RE in Chicago. By overall going long in equities that don't have much at all to do with RE in Chicago that could offer some balance. Instead of selling calls on my equities since I could risk unqualifying my dividends I sold 2021 Dec straddles on the SPX to hopefully provide the same volatility decrease as covered calls would. But also opening up the opportunity that if my equities dropped my SPX short would be profitable and since it is 1256 I could take the short profit at a high % of that as long term gains. Now we are in Feb 2020, my strategy didn't go well on the equity value side. My "defensive" equities literally plummeted, while the SPX boomed delivering a double hit. Almost all of my 400k gain was wiped out. Today I am hovering at about 20k over my Oct 2018 entry point. I did achieve some of what I sought on the 0% tax bracket. I think where I went wrong was largely the short I chose to hedge my dividend portfolio against. I was hoping ET community could offer up some recommendations. Inevitably with seeking a high yielding portfolio, I do have a substantial portion in Petrochemicals. I tried my best to balance this with other sectors as well. Currently, the dividend yield on my cost basis is 10%.