I owned an outdoor power equipment business for 31 years, so most of my experience is with small air cooled, high rpm equipment, not outboards. that being said..... I sold Optimol products (
2 cycle oil ) in my own shop, which is a high ratio, high quality oil, much like the Amsoil is targeted at. I sold Stihl and Husqvarna saws to the local loggers and many of them used the Opti oil from day one after purchase with phenomenal results. it was once typical for Pro loggers to trade in or scrap a saw within 2-3 years at best, but with the Opti they were easily doubling that.
The only place I saw any problems was when a customer would switch from 32;1 or 40:1 to the Opti on an old tired piece of equipment, against my (and the factory reps) recommendation. Problems could arise from the normal carbon that had built up in the cylinder head, and on the piston top, with the rich mixes. when they switched to the lean mix that hard carbon started breaking loose and plugging mufflers/spark arrestor screens etc, and in a couple cases actually scoring cylinders.
Cool running water cooled, and low RPM, 2 cycle outboards don't have anywhere near the tight tolerances of high quality saws so it's almost an apples and oranges comparison. but it's my humble opinion that outboards need more than even the best 100:1 mix oil can provide to survive. I own two later model 4hp 2 cycle Johnson outboards and will not be switching from the quality 50:1 that I use now.
As an aside: when I owned my shop I constantly had customers try to convince me of their rational for using the cheapest 2 stroke oil they could find at x-mart. "oil is oil. what difference does it make" being the typical argument. well it's NOT just the base oil that matters. it's the additives that are in the oil that determine it's protection qualities. it's my opinion that the most expensive oil out there is still the least expensive way to extend the usefull life of an engine. not only will a high quality 50:1 protect the engine, but it will smoke less and run cleaner/stronger than a lower quality oil as well
Just my .02 from a tired old grease monkey