The question was how to size the transformer. In addition to specifying a bigger transformer, there are various industry standard 'tricks' that many have specified before ..
I believe that ANSI standards requires a substation type transformer be able to sustain 125% of its nameplate rating for one hour. Then there are the 55/65 degree rise [another 15%] that one can specify for liquid transformers to run cooler as well as prepare for overloading. [The ventilated dry transformers based on Class H insulation can have ??% additional loading [I seem to remember it was 25% but not sure] if one specifies 80C rise instead of 150C rise].
Then there are fan cooling, and ANSI has specified the extra loading allowed when they are specified. [Sorry, I only remember 33% for Class H vent dry transformers].
I agree that it is more appropriate to look at the loads first, essential vs. non-essential, etc. Then the thing to do seems to be fans. And if you would like to baby your equipment for longer life, the 55/65 or 80/150 rise thing can be considered after that.