Frictional pressure losses in pipe are very dependent on pipe diameter (as you imply).

It is also fairly dependent on flow rate. Sometimes bigger is not MUCH better, especially if you are trading off money for time.

Pressure drop estimates for 300' run of plastic pipe:

Diameter GPM Pressure Drop
2" 300 169#
3" 300 24#
4" 300 6#

2" 200 80#
3" 200 11#
4" 200 3#

Those are ballpark estimates for straight pipe only. I hope that is sufficient information for you to start planning your project.

Those figures are for the frictional pressure losses only. You will have to add in the additional work required from your pump to lift the fluid as required for your elevation changes. (In general, place the pump as low as possible on the suction side to your water source. "Pushing" the water is usually far more efficient on the discharge side, relative to "sucking" the water on the intake side.)

Good luck on your project!