It sounds like you may have a couple of concerns. If you write a covered call on stock that is already long term then no problem unless your concern is tax year and it's obviously late in the year for that. If the stock isn't long term and you want to hold it long term avoid selling an ITM call as that will freeze the holding period. You'll want to sell a qualified covered call and you want to google that term. Usually thought to mean well out of the money. You can substitute stock if you choose when you receive an exercise notice. You can buy you call back anytime prior to COB. So if you sold the $55 call and the stock is trading over $55 at expiration you will be auto exercised unless you advise your broker to not auto exercise. This does assure you won't be exerciseD as you broker may still receive exercise notices on all their short option position. Obviously you can also be early exercised because of dividend/carry issue or just stupid exercise. Say you get one and you don't want to deliver you own stock. Stock settles T+2 and all exercise occurs after the close. Many broker will all you to buy stock and same day. You want to have this discussion on what your broker allows and what it will cost because you are going to need a physical help desk and it's going to be expensive(almost not worth doing and especially not worth doing for a modest dividend). OK you get an exercise notice and you want to keep your original stock and deliver a new lot bought same day settlement. Expect to see a dividend paying stock trading cash without the dividend and your costs and the price you buy your new lot for to be away from the current market. So it almost doesn't pay - but it can be done. Figure out if your broker has the ability, what it will cost and obviously you will need enough buying power in your account to same day settlement. A couple of points - don't be unreachable near expiration or the xdiv date. Even if the stock tanks the next business day your exercise notice is still good you just got lucky. If the stock rallies big the next you'll still be buying at the new price. Read carefully the definition of a qualified cover call. Put yourself into the mindset of a naked call writer and really actively manage your short call. Essentially you are just a naked writer who just happens to own the stock. The event will generate an ordinary income event and most often not worth it just to keep the favorable tax status.
Why would there be any realized capital gain on the stocks if you buy back the option and the stocks are not actually sold/called away? I understand I would have cap gains on the premium if there was any left after the buy back (doubtful). What am I missing here?
Stocks and options cap gains/losses are counted separately. If your stocks are called away and that resulted in a capital gain, you would still be responsible for that too. If you closed your short option position that would not result in any possible assignment, then you have nothing to worry about. Again for details, ask IRS (if you are an American) and/or your accountant.
IRS workers are paid the minimum federal wage, and barely have high-school diplomas. Better off going to the CPA. Trust me on that.