What is that oil lubricating? I'm a total newbie at this, but love projects
there are 3 separate gear boxes on a stringer drive. the intermediate on the back of the motor, then the upper and lower on the outdrive.
the oil could be coming from the upper or lower. its entering the water cavity.
it could be a simple seal, it could be a gasket, it could be a cracked housing or something else.
the problem with an outdrive, if it leaks oil out, it also leaks water in. and gear boxes do not survive with water in them.
from fixing a stringer on family boats, expecially the upper gear box only takes a few hundred feet prior to welding the bearings together when the oil level drops and water is allowed to make it in.