I am happy with recent bull market. However, my calls (SPY) I sold are very deep in the money now and will be expiring in 3 weeks. If it gets called away I will make profit. Long term capital gain (in the 37% tax bracket, no state income tax).
I am wondering what my options are:
a) Roll up; I buy back the call at a big loss and sell another call which would supplement the current loss premium. The call would be at least 8 months out. Pros: I can defer the tax gain until next year. If the market stays sideways or goes down I should be OK. Cons: The market keeps going up until 8 months -- which is fine I suppose.
b) Let it get called away; I would make a profit. I then DCA into it monthly. Pros: I will have cash. I can reallocate. Cons: I would have to pay LTC (taxes) which I would like to avoid. I also loose on the all the gains in the past month -- which is fine.
I am leaning towards rolling up. Anything else I am missing?