Boat's on the trailer that way so he can lift the tongue! I use a fork truck to lift my steel boat ! (and you're not going to hurt the bottom or transom on this one!)
Motor.. as many have said has seen some rough conditions, but that said the old 9.8 Merc (about the same vintage) I have in the boat house was a rental, looks worse than that one, cowling sits crooked, engine filthy.. RUNS LIKE A TOP.
WATER TEST long before a dime changes hands.