I think the smart man who wanted to throw off people searching for him would pick a place where he could make it look like his vehicle became disabled unintentionally.
It would not be too hard to set such a thing up. Then drive away from the damaged vehicle after leaving several items of value inside to make it look as though you had to leave the stuff because you could only carry so much.
Wouldn’t need to be an Einstein to figure out this sort of a ploy.
So, he also purposely fouled the prop with a mooring line on the boat he started to take from the marina - another clever feint?