Maybe you're over tightening them?
I've always just hand tightened them and then snugged them up.
I've never used anything on them.
You're not dealing with any pressure to speak of.
Welcome.
A serial number would help as there are 2 possible systems for that era.
A picture of where the leak is would help as well.
Can you describe this "housing"?
Is the pump in the boat or is it part of the motor?
I have a 1974 and 1980 version of the 3.0 and neither have a block drain at the rear of the starboard side.
They do have the oil pressure sensor in that area.
I always travel with my kicker attached.
I put the the motor in the down position and in reverse so it won't bounce up.
I also strap the kicker leg to the transom to help with bouncing.
I'd check it against another tach.
There might be a selector switch on the back for different pole settings.
Try clicking it slowly through all the positions a few times.
Sometimes that gets them working properly.
I'd have no trouble running it. Just make sure you drain the block and
manifold afterwards.
You can run a water hose directly to the motor.
You should be able to see a hose running from the transom over the intake manifold to the thermostat housing area.
The hose is the size of a heater hose on...
I'm not familiar with that model but that's a lot of boat for a 3.0 and I'm a fan of that motor.
It might not be enough motor depending on what you want to do with it.
Maybe try a different oil.
I know when I switched to synthetic the apparent smoke at startup was less.
Could also try putting eau de bacon in the oil. Then no one would complain.