Help with building a hedged value dividend portfolio

gescob3 said:
Yes my account was up 400k, at its peak in April of 2019 so a very short time from when I entered in Oct of 18. My goal wasn't trying to ironclad protect that gain per say, but overall create a steady stream of around 100k/yr in capital gains.
I don't think the premise was flawed just my chose index hedge didn't move with my smaller cap value portfolio.

I was wondering if someone might have a better idea of 1256 index to use instead of SPX.
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Yes;
find something better than Argentina banking[ great country], oil + gas stocks ............................[50% in those is asking for even more trouble/flawed].I like some dividend stuff also; but not so much, in an early bull market or as way to avoid downtrends.
''Value'' stuff in stock market tends to get less valuable. Great country to visit=Argentina................................................................................................Hope this helps; it helps me.
 
gescob3 said:
Yes my account was up 400k, at its peak in April of 2019 so a very short time from when I entered in Oct of 18. My goal wasn't trying to ironclad protect that gain per say, but overall create a steady stream of around 100k/yr in capital gains.

I have very complex tax returns, in short I have had a negative rate for several years now. If I took a 400k gain all at once it isn't just the taxes I would pay on that gain, but it would also negatively hurt me on a lot of other mechanisms I have going on. I can handle a trickle just not a windfall.

I had an audit this year where the IRS made a mistake a number on a calculation and I needed something to be exactly below a very specific number to avoid a lot of phase outs. The difference in $200 in income swung me from a 5k to refund to owing 6k in taxes. In the end once I had someone from the IRS on the phone they corrected the mistake within 24hrs and then I got my refund.

My overall thinking was to have a long equity position that generates qualified dividend capital gains and short 1256 contract position that I assumed would move in the opposite general direction of my long equity. Back in April when the SPX was at 2875 I decided to do a long term short SPX LEAP structure where my break-even would be at 3750 by Dec 2021. Anything below that I would make some pretty substantial profits. My safety against the SPX rise would be my long equity position. I don't think the premise was flawed just my chose index hedge didn't move with my smaller cap value portfolio.

I was wondering if someone might have a better idea of 1256 index to use instead of SPX.
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Forget what I said/suggested. Professionals who trade for institutions are in a better position to advise you.

I am just an amateur retail trader, not a tax accountant so it is very difficult for me to understand what you are trying to do let alone advising you. :wtf:

I am in the minor league, I trade to make money, to make a living, not to avoid tax. My wife has a general requirement regarding my trading career: Make sure you pay tax, the more the better, I don't like tax losses.:finger:

Best wishes to you.
 
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