Quote from chrismontez:
Well I guess that depends on what you think is a good return on your $. If your exit strategy was to sell your stock when it hit $30 and you can sell an ITM call that would give you an additional 10% return, I don't mind tieing up my $ at a 10% return. I've got cash sitting in accounts that pay me less than that now.
You are making kind of an assumption. If the stock is at $30, I doubt you can find a deep ITM call for a few months that will give you a 10% additional return unless you pick and choose how you are defining that return. If you sold the stock at $30, I agree you would not make an additional 10% sittingin cash. But a deep ITM call will not give you an additional $3.00 of profit either which is the additional 10% you are comparing.
So you cannot say 10% more is gained selling a deep ITM call that is 3 or 4 months out in time.
Here is a close example. EBAY is trading at $28.17. If you sell a $20 strike call for JULY you will get 8.70 in premium or an effective sales price of $28.70. Is that extra $0.53 worth tying the money up for 5 months and capping your upside. If you sold you can take the $2,817 and invest it elsewhere. Deep ITM calls can also be construed as constructive sales so it will not work to delay a sale to get over the 1 year short-term cap gains hurdle. I used to think otherwise but was corrected.
Now you can sell the $30 JUL Call for $2.25 or perhaps the27.50 Call for $3.50 to add some more profit with ATM or OTM calls which gives you a little profit boost, but still, you wait 5 months for that extra profit while tying the money up. Would be better with those strikes then the deep ITM call in MOST cases.
Selling a deep ITM call against a stock position in most cases does not make sense except for maybe a short-term hedge. Even then a protective put still allows for upside.