I have a question that I’d appreciate your input or thoughts.

What, realistically, is the chance/risk Berkshire holdings could result in a large, forced capital gain for us—years down the line post-Warren?

In doing estate planning, I’m looking at possibility of gifting low basis Berkshire shares to my son to remove from my estate—part of overall strategy to reduce my estate taxes. This would be a limited number of shares..my son has no intention or (hope) presumed need to sell before he then left shares to our granddaughters with basis step-up

I understand the real life family risks here—but the one risk I can’t quantify is THIS. I’m ok with a distribution from a subsidiary holding here and there, even a large one (which I fully anticipate btw at some point in the next 50 years).

This only works as a generation skip….because my son otherwise would inherit shares with step-up and they are very low cost basis. But inheritance tax is 16% here at the margin—so moving this stock plus its appreciation over maybe 20 years would reduce estate tax by a few hundred K

Has anyone else looked at this essentially generation skip strategy? Or are you, unlike me, not stupid enough to live in Massachusetts and have no need :)