If I've sold cash secured puts and they're in the money at the close on Friday, then I'm buying stock. If I've sold covered calls and they're in the money at the close on Friday, then I'm selling stock. And if they're out of the money on Friday, I'm a happy guy because I'm going to keep all that premium money. But what I'm not doing 99% of the time is buying the option back. That's not the direction I want money traveling.
If I'm the new owner of stock because someone "put" shares to me I'm usually looking to sell a covered call the following Monday morning. If I've lost shares because someone has called the shares I own, then I'm looking to sell cash secured puts the following Monday.
I would prefer the options expire worthless on Friday afternoon but I'm prepared to execute the above processes, as necessary. It's worth the exercise to generate the extra options income which supplements the income I receive from dividends because it's often double or triple the amount normally received from the dividends alone. By reinvesting the money those options provide along with the dividends I receive, I can build up stock positions faster than by using just the dividends. And it's building up my wealth just that much faster.
My favorite options are any options that expire in one week because the steepest decline in the premium occurs during that last week before expiration. Those one week options also limit my exposure to the inherent volatility of the underlying security by limiting my risk exposure to only one week. Finally those one week options will allow me to sell options closer to the actual price of the security and obtain the maximum deteriorating premium. It's all about deteriorating premium for me.
In cases where the premium is basically nonexistent for one week options, my next favorite option are those options that have two weeks left before expiration (my third favorite are those options with three week left before expiration). My preferred strategy is to sell options with strike prices as close to the current price to maximize the premium and options with very close expiration dates to minimize my exposure. And then to sell those options over and over and over again.