Specifically how and where are these Baggers always leaking from?

Yes, it bolts to the side of the trans gears etc. If not vented properly.

 

Nice gear set.

 

For all the engine issues Harley seems to have, their transmissions are somewhat bulletproof.

 

That looks heavy.

 

When the rest of the bike weighs 800-900 lbs, it’s relative.

 

You haven’t been on an old tractor lately have you.

 

Trivia: Big Twin engine weights, from my 1988 FXRS-sp (Long gone - was a good street bike):

Transmission assembly: 35 lbs
Primary assembly (Cases, clutch, chain, compensator sprocket) 40 lbs
Engine: 125 lbs
Electrics (Starter and alternator) 15 lbs
Total 215 lbs.

Some other engines (With starter and alternator, no carbs/EFI or exhaust) that went across the shop scale:
Honda CBX: also 215 lbs
Ducati 999S: 156 lbs (A lot heavier than I expected)
Kawasaki EX500: 126 lbs (Also a lot heavier than I expected)
1988 HD 883: 185 lbs (1200 is a several pounds lighter!)
Kawasaki KX500: 60 lbs (Another reason why I like 2-strokes)

Those pictures of the transmission with the lid off brought back less than fond memories from about 25 years ago of replacing entire transmissions out of Softails around the 30,000 mile mark like clockwork (Which few did) due to broken shift pawl springs. They would develop a notch from rubbing against the centering plate (Wouldn't have been a problem if they knocked the sharp corner off the plate, but, hey, production costs...) and the broken off end would drop between the spinning 5th gear set. And since HD upgraded the gear tooth geometry to a "High contact ratio" (For noise reasons), they ran out of old replacement gears quickly, which meant the customer had to buy an entire gear set (The old gears were incompatible with the new gears).

The primary breathes into the transmission - if the transmission breather is pinched or plugged, the clutch cable is the only escape. Somebody(s) screwed up.