Things start easier with the kill switch in.
That's what happens when you never take the rig out of the garage, haha. You need more practice.
I have done several things, my biggest mistake was not putting my motor in neutral on my first hunting trip after switching from my Godevil rig to my Mudbuddy. After setting decoys out, it would not start so I pushed the boat over to hide it worrying about it not starting all morning till I figured it out after the hunt.
Another solo trip, I tied to a 4" wide tree about 8 feet long and forgot to untie after the hunt, when I got back to the ramp I notice I was dragging it the whole time, boat still ran fine though.
In a hurry one morning, forgot to remove tie down straps on the back so it just floated the trailer, felt pretty stupid about that one.
You will have more stories if you take that thing out of the garage.