For most...towing a dinghy, motor or no motor is a real non-starter.
You guys are funny, or maybe just parochial. Towing a dinghy with a motor is quite common here in New England; everything from 9' inflatables with 5hp outboards behind 27' sailboats, to 36' center consoles towed behind 250' motor yachts. Sounds and bays like Vineyard Sound, Buzzards Bay, and "open water" like Massachusetts Bay. Yea, we never have waves or heavy seas or storms here, that's all just legend and myth.
Let me be more specific. If you have a 36 or 38' sailboat, or even 40 or 50, and you also decide to have a 9 or 10' RIB with a 15, towing is the only sensible option.
You occasionally hear a VHF call about a lost dink; but in my experience, not even once a year.
Mine is towed with a webbing towing bridle, and the painter from an eyebolt on the bow is tied to the tow line, i.e., up past the snap that secures the bridle. The only single point of failure is the main tow line, which gets inspected ever time it's used.
I have never, ever flipped my RIB, and have never seen one flipped, or heard of one flipped, in my area.
It could very well be a regional thing, but that's the way it is up here, and has been for the last 20 years.
I, frankly, couldn't be bothered hoisting a motor, and deflating and rolling an inflatable boat for the kind of cruising I do. If I was making a crossing, certainly, I wouldn't tow; I might not even bring one. There are times I was in harbors in sloppy weather and I wouldn't have been comfortable in a non-RIB with a 4 or 5HP motor.
Suit yourself, but towing my RIB works very well for me. Maybe in Florida it doesn't, I wouldn't know.
Every single day of the season at least several dinghies are lost or flip when being towed here in the Windwards. Every single day.
Really. "Every single day." That's quite remarkable. How do you know? Are these incidents reported somewhere? VHF traffic? Or maybe there's a database of some sort? That must result in a large market for dinghy "harvesters" and a huge used dinghy market, no? The flip side is that if so many end up this way, there must be an awful lot of people who are towing dinks, and a proportionately large number who's dinghies don't flip or get lost. Make sense? What do you think the rate of lost or flipped to successful trips might be? Of course, people wouldn't be making a report, or a VHF call, or updating a database when nothing happens, so we wouldn't know.