How much gear oil should they take? I started from the bottom end
squirted until I saw oil from the middle outlet, closed it off and tried
to squirt some in from the top, no go ??

If you are talking about an OMC Cobra drive, there is no middle outlet. You
may be mis-identifying a water drain fitting, located above the lube vent
fitting, as the "top" lube outlet. In other words, I suspect that what you
are calling the middle outlet is actually the top outlet.

Dry wrote:

How much gear oil should they take? I started from the bottom end
squirted until I saw oil from the middle outlet, closed it off and tried
to squirt some in from the top, no go ??