Why all the concern about using big transformers to drop all the way to 208? A small 2kVA 32v buck transformer is all that is needed here. 277v-32v is 245v. Good to know that the model 3 does support 277 natively though.
2kVA is not enough for a decent charge rate on a Tesla. I assume you are referring to the rating of the transformer when not used as an "autotransformer" (in which case as an autotransformer its rating will be many multiples of the 2KVA).
It is still expensive to need a transformer for each EVSE (or to put multiple on one transformer). Much easier to just hook to 277v if that is available!
I agree with @wws that SAE should extend the J1772 spec to support 277v. I don't see 277v going away and it just seems like incorporating this to the standard would eventually allow its use once new vehicles cycle out and everything supports it.
Unless the increased materials cost to allow 277v was prohibitive or otherwise unsafe?