Thanks for all the responses, I think they were as helpful as any I've sought here in the past.
Conclusion:
What I hadn't mentioned was this was all for a temporary setup - a temporary 300T chiller. Since it was temporary, I was willing to cut the contractor some slack in the submittal. The mechanical contractor had informed us the 300T chiller was only available in 480 (460)V, and the facility only had 208V, hence the requirement for the step-up xfmr. The chiller itself only required delta power, but it had available single phase and single pole (277V) aux connections, which I wanted to use for the temporary heat tracing. Ultimately though, I lost that battle and they're running temporary 120V circuits about 200' from inside the building, down multiple corridors, through a temporary construction opening, to the temporary chiller, all for two heat trace circuits which could have been powered from right there. But, that's means and methods, so whatta ya do? I just said fine.
But, as a result of other conversations related to this matter, I lost confidence in the electrical contractor's prudence, capability and reliability, and took the hard line and required a submittal that met the design specifications. At that point (losing the heat trace "battle"), I wasn't about to go back and say, okay, never mind, delta:delta will work after all. Given all we've been through with this lowest bid contractor, I wouldn't have put it past them to come back at a later point and say they needed the 277 after all and try to scratch out a change order. Of course they'd have ultimately failed to win the change order, but with all the effort associated with contesting it, I certainly wouldn't have considered it a "win" for us.