There is a voltage drop over the entire roundtrip distance of the circuit. Running things from the pole to the pressure switch in the house isn't going to do anything that just feeding it from the house is going to do. If you could mount a pump controller or just a contactor out at the pole, you might be able to get by with smaller wiring due to the much shorter run.

Have you considered using one of those pumps with a VFD? (Essentially, it makes an artificial 3-phase from your 240 single phase). Works real nice.

I had exactly the same situation: pole (and meter panel) 200 feet from the house, and well in between. My contractor fed the well from the house, running the wire in the same trench as the main feet from the meter panel.

One thing to consider: the pipe from my well to the house just went bad (55 years old). My contractor installed 2 new pipes and ran the wiring through one of them. If the water pipe ever goes bad again, they can simply connect the pipe with the wires to the water, and run the wiring through the bad pipe. It will save me the cost of having my whole yard dug up again.