Still holding some DITM Jan. '24 BRKB calls. Debating rolling them up and out vs. locking the 30% long term gain. Closed out some of them a couple months ago, but who knew price would drop >7% (Arghhh!). Please share your shrewd thoughts and weigh in on this dilemma :) Thanks!

I've rolled or sold most of mine for that date, but I still have some. I'm going to roll them some time soon, I just haven't got around to it. (and also watching what interest rate expectations do)
The best day to roll calls out (or out and up) is when that the stock price is highish, anticipated interest rates are lowish, and the market is calm.
Other than the fact that interest rates are not super low, last week would have been fine. Mid September even better.

On the other hand, if you're just going to sell them outright rather than roll them out, just go for the highest stock price.
The ideal for that, unlikely to be seen, would be a day with high stock price, high volatility (often panicky market), and high anticipated interest rates.

Jim