Holley recommends to put them at or below the tank exit to put less strain on the pumps. The pumps go after the water separator filter, which can be higher but again low is better. Basically after the filter and pump are full of fuel there won't be much of a lift problem for the pump do to lines all being full, and another reason for the anti-siphon valve at the tank.
I would use no more then one filter inline, but the one on the carb inlet is not an issue.
I would add a Tee to the oil pressure port and add a 3 prong switch and wire like the pic below.
Do you have 3 or 4 terminals on your starter? (2 large, and 1 or 2 small