Well, ill go ahead and check the gear oil and go from there.
Outboards have one operating feature different from most 2-strokes.
That is, the exhaust pipe is a couple feet underwater. That water column creates pressure, which impedes the free flow of exhaust. This resistance could be overcome by running the motor at a higher rpm, but then it would not troll at the desired slow speeds, as idle rpm would have to be high.
Manufacturers solved this by placing some small exhaust ports up high, generally just below the cowling. Thus allows exhaust to escape freely at low rpm.
As stated by the gator & Racer, 2-strokes never burn all of the fuel or oil that goes through them. This partially burned hydro-carbon creates blackish gunk, which eventually leaks out, wherever it can.
You don’t need to look at the gear oil for your issue, it has
nothing to do with what you are seeing. You need to go to Leroy’s Ramblings, (Google it), & gain a better understanding of how these motors work. You will discover A), how exhaust is routed through the lower leg.
B) the two small holes do drain water.
C), they often weep gunk, especially if the motor is used at low speed for extensive periods, or run rich.
D), look just below the last post in the thread, you will find dozens of threads questioning gunk leaking From small holes in the leg.
http://www.marineengine.com/boat-fo...483-Oil-coming-from-small-holes-in-lower-unit
This shows it graphically, if you’re in a hurry, scroll down to about 2/3 way.
https://leeroysramblings.com/Johnson 9.9_15.htm