So I think what I'm going to 'counter propose' to the well guy is (they seem to have a Goulds preference) 5GS10 1PH in the well (I assume that will need to be down pretty deep, not sure there), that will fill the ~ 600 gallon cistern tank in the basement. Add a 25HS10 to the tank (with the float switch etc) then a PK1A Pside Kick outside the tank for the constant pressure. Sound perfect? Maybe the 25HS10 is overkill and the 18HS10 would suffice.
Depending on where their pricing comes in if I have $ left I might have them add a PK1A Pside Kick before the cistern with extra valves to handle the situation you highlight that the tank pump dies and we need a temporary alternative.
I have a feeling I'm going to have to send them the diagrams from your site