Do you lift it with a tackle and then slide it in? Also, have you ever been in conditions, say you've returned to a now exposed bouncing anchorage, and the stern is going up and down?

It is a good idea though, especially for a large outboard. Those things look like a handful for people when conditions aren't great, to get onto their stern rails. It wouldn't be wise to tow a dink with a heavy outboard far, I'm sure.

I think the reason you've seen most boats on the northeast coast towing is, they're not going very far. Few boats venture more than 40 or 50 nms from where they're kept. Truth is, except for an occasional overnight, we rarely sail more than 10 or 20 miles. We don't have to as anchorages are not far away.