More fuel system questions

The filter before the pump should be the mesh "sock" on the fuel pick-up inside the tank. That's a fairly coarse filter and is low-restriction and will keep crud out of the pump. Then your fine particle filter should go before the regulator. Vertical or horizontal, it does not matter. Everything else looks/sounds good to me.
I don`t run one, my 3/8 intank p/up is a return line. I like to be able to turn the gas off, (valves) and change the filters.