Some of us live off our portfolios. We have no other income, and so holding just doesn't work, does it?

That's why Buffett detailed how to create a Berkshire dividend. So, if you're gonna be selling shares anyway, why not get an extra squeeze?

Well, because there's additional risk involved. If you sell 10 BRKBs every month for income, you get ~10*500, or $5k a month. But if you sell 4 530 calls each month for $13 to get the $5k, once in a while, the stock will pop suddenly and you will get assigned on those calls and have to sell 400 shares all at once, possibly at a less attractive price. In a rising market (and by definition, when your out of the money calls get exercised, you are always in a rising market), you may end up with a pile of cash not working for you anymore. So sometimes it's a choice between selling a few BRKBs each month and being "forced" to sell a few hundred at an inopportune time. That's why.

And, yes, while you can buy back those calls, that means you have to leave a rather large pile of cash available to do so, AND also have to sell some BRKBs each month for income.

That isn't to say that it isn't a good idea to sometimes sell calls or puts. It is saying that one should be fully cognizant of what selling an option really means. I only sell options when I truly want the consequences of that contract (each option is a contract) either way. I sell puts on a regular basis on stocks that I already own and am willing to increase my position in them at that price (a few days ago I sold some puts in DIS and in AAPL at prices that are attractive to me).. And I periodically sell calls on stocks that I own at prices that I am willing to sell those stocks. Using puts and calls this way is mainly to get better prices at purchase or at sale, and sometimes those options expire worthless. In my internal tracking, I use the premium received as an effective "reduction of basis" or simply as part of my tracking overall IRR for that stock.