And electricians out there

Yes, you want to plan to stay under 80% of the rated capacity. Run some #10 and use a 20A breaker for possible growth. Put a 30A at the pole.
I guess it would maybe easier/cheaper to leave the well feed right off the box at the pole like it is already, and put a 30 amp breaker in the pole box and run a wire to a small box and 20 amp at the shed for the heat lamps?