The fuel pump runs with the PRESSURE from crankcase compression.----That is not the same as compression in the cylinder !-----There may be an issue with crankcase compression and fuel pump does not work !-----Mix the fuel at 50:1 in the portable tank.----Have your assistant operate the manual...
Friends of mine had one of these motors on a 17' deep V boat.----Skied many miles behind it.----Used to pull 2 skiers out of the water with slalom skis.----A real powerhouse.----Take starter apart for inspection.-----See what it needs.
High speed jets are an orifice plug.-----Not adjustable.----Perhaps you can experiment with different jets to compensate for fuel.----And local atmospheric conditions.----If fuel consumption is a major concern ,this is not the motor for your friend.
????-After the pump that hose does not pull air in.------The earlier V-4 models mounted the pump on the carburetor air box.----They needed a third nipple and hose to provide a PRESSURE pulse to the pump.-----These pumps are very reliable and very simple.
I visit 1 yard with many scrap/ not worth fixing boats.------But I know there are many folks who think.---" it is fiberglass , nothing can be wrong "-----Little do they know of the junk wood in them.----Or shoddy work under the floor !
What you are seeing is all normal for that 2 stroke motor.----The hole is put in to drain the casting cavity.----The leaking oil is the oil you mix with the gasoline !!