So it's not leaking around the pump at all, I cycled the valves and saw nothing there and when running the pump after adding water it performed perfectly. Shut off right away every time, no issues. But I do think there's a leak at the intake from the fresh water tank that I'll have to look into. Once I added water back into it I did see some dripping from the underbelly. So I'll have to pull that material down so I can see the tank and both the fill and pump intake line.
On another note, there is a sediment filter between the winterize valve and the pump but there's no filter in it. Does that make any sense??