I am not looking at the book right at this moment but I believe the bushing spec is on the order of .001. As long as it doesn't leak like a sieve .002 probably would not be a disaster.
It's .001, which is fine, but the problem, and Harley knew this by 1939, is that there is a constant whip-action on the mainshaft from the primary drive torque, that acts on any freeplay between the mainshaft and bushing. The more you drive it, the greater the freeplay becomes. Yep, alot of the oil that lands on the ground is from the chain oiler and the impossibliilty of a stable needle-metering-ability, and the fact that the primary chain needs gobs of oil or it will stretch prematurely. ( I use to have my S&S pump needle on my '59 Pan dialed in to where I would only have two quarter size drops drip to the pavement, if I left it parked for a few hours on the jiffy stand, which is nice, but I would go through primary chains every 3.500 miles!
What we did was to change the MDG bushing to needle bearings. So when we spin the needle bearings on the mainshaft, they spin like a roller skate wheel. There are two sets of needle bearings now for lineal support that the bushing didn't provide.
As far as the 1-1/2 pints of oil, that's okay. If 1-1/2 pints of oil doesn't cause the oil to drain out past a worn MDG bushing when the machine is parked on it's jiffy stand, great. If oil does drain out when on it's side stand, no big deal either. Set the bike upright and check the oil. If you can see the oil pooled down at the bottom of the trans, your okay too. Like Jack said, "checking the trans. oil level before a ride is part of what you do".