I only leave it on the trailer until I get to the ramp, then I slide it off and go fishing
, unless I have to break ice first. As for the motor position, I use a transom saver, to support my outboard. It takes the weight off the pistons/transom, you just have to remember to remove it
before you launch or you buy a new one after you put the motor in gear and it cuts through the bungee cord holding it on the lower unit.