If you need/want to run the
engine before you haul, use an extraction
pump like is used to pump the engine oil out thru the dipstick tube.
Pump out as much as you can...I aimed for about 1/3 capacity on a SD20...fill with new. Run lightly in
gear for a couple of minutes, and repeat maybe 8 times.
Oil should look pretty good then, unless you have a really bad leak.
If that's the case...and I've never had to do this, but maybe you could modify the fill cap with a tube and provision to SLOWLY force oil into the housing by having a header tank several feet above the waterline. Once you have injected enough oil to fill the housing, lower the tank until it's maybe 6 inches to a foot above the waterline to control the oil leakage. Don't want to pollute if you can help it.
I'd get the oil as clean as I could, and use this
motor only for maneuvering.