Considering we have different brands of JPs, it is hard to say. If I was maxed at 3.5" and no lower then I would go to the first hole. I would just leave the JP raised up a bit so I cleared the rigging/steering when towing. On hole 1, you would be closer to 4" PTP and could raise the motor to whatever. I spoke to Atlas a few years ago about whether or not I could keep the JP raised while towing and they said it would be ok so long as my transom saver was attached. Considering I was already close to 4" PTP on hole 2, I just left it there so I didn't have to worry about me smashing my hydraulic steering.