The problem with bringing primaries up to a building is having the right of way, most utilities will not bring their primaries without a right of way given to them for future access in the event of a failure, the only other way around this is for the owner to pay for his own transformer and conductors which can be very costly, the other alternative is to size the conductors to minimize as much voltage drop that could be achieved, having 1/0 across the road is only part of the circuit which if short enough can allow you to provide the remaining run with large enough conductors to over come any voltage drop on the remaining run, with motor start up current sometimes it can be impossible even setting the transformer right at the load specially if the POCO sizes the transformer small which is very common, I have seen many 5kva transformers set for 200 amp services and not too un-common for a 10 kva to be set for a 400 amp service, and there is not much you can do if that is all they offer if the voltage drop stays within your states adopted limit which can be +- 10%
Also depending upon the type of lighting installed you can get lighting that does not flicker when the voltage drops such as non-dimming CFL's as they have built in voltage regulation and do not very in light output over a much larger voltage range, I had a very noticeable flicker in my office every time the heaters in my laser printer kicked on and off but since I put CFLs in it no longer happens.
To even figure how large a wire you will need to run will need a few bits of info:
size of transformer set
how long is the 1/0 run
max demand load expected
will you be running aluminum or copper aluminum will be much cheaper and can be sized properly even against copper.