Ok so lets say we want to design for 5% VD at 100 amps, 240 V (24KVA) That should be plenty unless they have something like an on demand water heater or an electric furnace.
I get 600KCMIL AL at 240V with 4.5% VD. At 480V, I get 1/0 with 4.3%. BUT, that is ignoring the voltage drop of the transformers. You actually should pretty much double that, maybe around 2% each, so really you are at 8%. Now lets go back to the no transformer route and plug in the 8% and see what we get. Looks like only 250 is needed. And dont forget the $300/yr in no load losses.
People always ignore the transformer VD and losses. I have a step up step down at my house (1900 feet) and trust me, it is not a great way to go, your voltage will swing a lot more than you think. I would never entertain doing that for 1000 feet.