Here's my problem with the "wouldn't mind losing some shares" line of thinking. I think I am willing to part with shares for $1000 this month. I don't expect the stock to stay at those heights for long. So I picture it squeezing over $1000 on or about the 18th and then falling back to $700 or a similar lower range the following week.
But what if the price shoots up like that and the option isn't exercised? I would want to sell a block of 100 shares then, while the price is temporarily still that high. But then what if it IS exercised just after I sell my 100? I don't want to lose 200 shares at that price! I have a higher target for the next block! Or what if there is a "slow and steady" rise to $1000 and it doesn't look like a squeeze after all, and I decide to hang on instead of selling in anticipation of a drop?
Bottom line I feel like the "I'm willing to part with shares at that price" doesn't play that well with selling calls to make the transaction if there's the chance it will take a short-term squeeze to get there. I don't think the $770 premium for a Dec-24-$1000 call is worth all that juggling on a $100K transaction.
It would be easier if I was willing to part with shares at $700 -- but I'm not.