The first thing that comes to my mind is 310.15(B)(6)
For dwelling units, conductors as listed in 310.15(B)(6), shall be permited as 120/240-volt , 3-wire, single phase service-entrances conductors, service lateral conductors, and feeder conductors THAT SERVE AS THE MAIN POWER FEEDER TO A DWELLING UNIT and are in a raceway or cable with or without an equipment grounding conductor. For application of this section, the main power feeder(s) between the main disconect and the lighting and appliance branch circuit panelboard.
I see too many times #4 THWN run for 100a or #2/0 TWWN run for 200a 3 phase pannels in my area.
With a 100a feerder you would meet the requirements of 225.6(A)(1) - #8 copper or #6AL unless supported by a messenger wire. Myself I would still use a messenger wire.
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At 40' will I need a pole between to maintain clearance??
That would depend on the drop heights and what your spanning. I would guess at least 1 side needs to be higher than 1 story.
Depending on your grounding situation you would need triplex or quadplex. Myself I like to uses an equipment grounding conductor even if there is no other metalic paths between structures. Reason is it's still safe if they create a metalic path later.
Based off 2002 NEC as I don't have the other versions with me.