I do have experience towing an inflatable who thinks he's a submarine. Its an old style dingly without tow ring so we tow via the life-rope. Big mistake. When the wind picks up and the boat goes 6-7 kts, the ding takes in water from its bow and started diving. Had to jump into the dinghy
and bail out the water before he reach periscope depth. You know what they say about a man on a sinking boat with a bucket is worth more than 10 Rule pumps
? What a ride!