For distribution transformers, the vast majority of the cost is fixed for things like the tank, bushings, accessories, and shipping, so upsizing from 15 MVA to 20 MVA may only cost a few percent rather than 33% more.
For evaluating transformer bids, I include factors for the expected lifetime cost of losses. For base loaded units, it can make sense to somewhat oversize the transformer. The oversized transformer will have lower I*I*R losses and will not have the fans/pumps run as much.
Lots of folks use the term DER, but the term DER doesn't really tell us anything about the operating characteristics of the plant. For example, saying solar PV provides obvious assumptions about daily load factor whereas with a wind plant there is an obvious correlation between wind induced natural cooling of the transformer and peak production from the plant. As an example of the variety of DER definitions, under the Washington State law (RCW 19.405.020) definition of DER, a natural gas generator is not a DER.