I was so hoping he would bust is rear

I can guarantee that an able bodied 45yr old man would struggle bigtime in getting in this way in 50degree water temps. I say 50% success rate. OK idea, though....

God Bless!

It didn't look like he had a power trim but a better way is to wrap your legs around the lower unit and then raise your motor and you up out of the water and then you can climb in the boat from there.

Yep, with wet winter gear such as coveralls you are at a big disadvantage. The best way I have found is to mount the motor and use the tilt/trim to pick yourself up and in. A boarding ladder is still the best idea.