Maybe.
Consider owners having a party, it is cool outside and you want the heaters on, but enough people are also in the house that the AC is also running. You want to leave them short on capacity in that situation? Might only be a few times a year but is the worst time for it to happen in customer's eyes.
I'd give them enough service conductor and overcurrent protection - let POCO take risks on transformer size - though they can usually get away with more in that aspect than you can with service equipment sizing