All good stuff. Yeah you will need to just drill a small hole in the pump check valve as there is too much elevation to make a bleeder orifice of any brand work. You can also add more than one air vent at the top if needed. An additional continuous acting air vent after the pressure tank should prevent any air from getting to the house. Instead of an air vent you can also just use a check valve on a tee that will let air in up top, but will close and not let anything out when the pump starts.