If this is carb outboard, then I suggest you break out some simple diagnostic tools. If this is fuel injected, you will need the electronic diagnostic program/tool to make sense of what is going on and then that will dictate the tools used.
1. Low pressure fuel pressure gauge, fuel T fitting, extra hose that fits on the outboard's fuel system, and hose clamps. The objective is to put this on to monitor fuel supply. You want the gauge to be on the line that goes to the carbs after the fuel pump, not before it.
If you're fuel supply starts to drop below the acceptable range at high speeds OR if an over pressure issue occurs, you'll know where to focus.
2. Timing Light. When aimed at the timing spot while the engine is underway with #1 spark plug used, this will show you the timing behavior AND it will show you the behavior of #1 spark. Once timing behavior is verified within spec per service manual, you can move the timing sensor to other spark plugs and see if a misfire occurs leaving an inconsistent gap of time before spark returns.
3. Spark plug socket and socket wrench to check the spark plug's colors to verify the cylinders are not running lean or very rich.
Time to get the detective hat out and get the outboard in a situation to act up with diagnostic tools ready to get data.