I need to lose $5000. (long term capital gains) in order to make over $20,000. Obamacare...

C

Cabin111

I've been in business for over 40 years (farm, rentals, stocks). In years I had large gains from the farm, I would buy chemicals or equipment to offset some of the gains (tax wise). Also I would try to work to match my gains with losses on the stocks if I could. And I (and many of you) would know where the tax brackets were and try to adjust accordingly. I get that...Common sense that my CPAs would help me with over the years.

Fast forward to 2018. I am 62 1/2, my wife is 60...We have to buy our own health insurance. Under Obamacare you need to be under $68,000. in order to claim the credit. My stocks, dividends, CDs, and other investments will probably be getting me close to the $68,000. threshold. We are investment/asset rich (Roth IRAs, farm, home, rental, CDs, stocks, deeds of trust), but cash poor. With CDs rising, my CPA tells me I need to not make any long term capital gains (stocks), unless I combine them with long term capital losses!! Also it is best if I don't take SSI now (not that I will), since that could push me over the limit. It is better for us to make $67,000. than $90,000. at the bottom of the federal 1040 form...To remain in Obamacare. In the end, we will make more money with the subsidy (over $23,000.)!!??? Go figure. Many of my covered calls went though in January of this year. So it's either sell some GE or Farmland Partners Inc. (FPI) for my loss. Thoughts??
 
You want to LOSE money??!! LOL That's easy. There are many ways.

1. Just go trade any instrument and put in SL of $5K

2. Put in a call/put spread option with $5K of spread

Good luck!
 
I could buy a put for some March 2019 Tesla stock?? Either make a killing or get killed!! I can't even buy 100 share of Apple in my trust account and do a covered call. They are sitting on so much money, you never know when they'll release it in the form of a dividend. This makes for strange tax planning.

Those of you not old enough, in the 60's and 70's estate taxes were really really high. People would do all kinds of creative moves to pass on assets to family members. My grandmother passed her entire estate to her adult grandkids (generation skipping) rather than her kids. You do what you need to do to avoid the tax when it makes sense...
 
What you really want is a trade where a loser will total $5000 but an unlikely winner will exceed $23000 plus the tax needed to pay on the winnings.
 
fan27 said:
What you really want is a trade where a loser will total $5000 but an unlikely winner will exceed $23000 plus the tax needed to pay on the winnings.
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Yes!! Or match up my gains with my losses so they zero out...
 
Buy deep OTM calls/puts on expiration day in weeklies in SPY. There is expirations every wednesday and friday. Just keep going until the $5k is gone.
 
Cabin111 said:
Those of you not old enough, in the 60's and 70's estate taxes were really really high. People would do all kinds of creative moves to pass on assets to family members. My grandmother passed her entire estate to her adult grandkids (generation skipping) rather than her kids. You do what you need to do to avoid the tax when it makes sense...
More...

One of the most creative way for you to gift somebody something tax-free is to actually make that person sue you and then you lose on purpose. Any gift then that is awarded to your intended recipient through a court judgment is tax-free. :) That's the law. Any money won through court judgment is tax-free. That explains why everybody loves to sue so much in America.
 
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