Your use of the word "there" has me confused, remember, we can't see you pointing to different places...
So you have power at an outbuilding near the well, so all you want is for someone in the house to be able to turn on the well from inside of the house, without having to run a control wire from the house to the outbuilding, right? Why is this necessary if he already has the pressure switch in the house? Or am I confused by that wording too? Usually, the pressure switch is looking at the water pipe pressure in the house. When someone opens a spigot, the pressure drops and that turns the pump on. So what is the wireless switch for? Is this a NEW system and someone put in the lawn before thinking about how the well was going to work?
If that's the case then, the problem will be with the concept of "reliably". In a well pump scenario like this, the pressure switch must also turn OFF the well when it is satisfied. If you use wireless, and the radio signal gets squirrelly, it can cause the well pump motor controller to chatter, which can destroy the pump and the controller. If you use a latching relay to prevent hat, and the radio signal gets lost, then it can run the well dry. Can they just put in a bladder tank system at the well, tied to a local hard wired pressure switch system? That way you don't need anything at the house at all, the bladder tank provides pressure for a time when the house needs it, then IT decides when the well pump needs to run to make up for the losses.