In the money Puts on BRKB

Jim, does it ever make sense to sell In The Money Puts on BRKB?

I guess.
If you want to buy the stock, but it’s not quiiiite cheap enough for you.
You definitely won’t buy at the current price, but definitely would buy at a slightly better one, and you’re willing to commit to that–
you’re willing to take a small cash bonus if it doesn’t hit your target price.

A fairly rare situation?

Of course, the relative chances of the outcomes, and the cash bonus, depend on the strike price you pick.
If it’s a very high strike price you’re almost certainly going to get the stock, at a price that’s only a teeny bit better than the current one.
If it’s a strike price near the current price, it’s a toss-up whether you’ll get the stock, but the cash bonus might be a fairly decent rate of return.