[Veserv]

No, that is not how the math works.

N is your cost basis. M is the gain. E is the estate tax. G is the gains tax.

((N + M) * E) is tax on the automatic step-up, option A.

(M * G) + (N + M - (M * G)) * E is the tax on the non-automatic step-up, option B.

Reorganized to ((N + M) * E) + (M * G) * (1 - E), it is clear that option B is strictly more taxes for any estate tax less than 100%.

[hunter2_]

:slaps_forehead:

Of course, it would be long term (20%) and estate (40% but on slightly less), not one or the other. Mea culpa.