I was more worried something was badly worn, wrong or missing causing the need for stacking washers. It could also be the wrong nut I suppose.. but more likely something is worn, crushed or missing. But working is better than right
I can stack washers all day. That's not what I thought would be wrong.
Thanks.
EDIT: When I took off the output pilot shaft flange, the nut was barely more than finger tight. Furthermore.. the brake flange bolts were also finger tight only.. or nearly.
I also found out what filled my brake with oil. The transmission was designed to leak.. that is.. it has a weep hole in the output shaft cover to let oil that will inevitably seep out not damage the parking/emergency brake...
WELL.. there was a big hunk of felt in the weep relief cut. Filled the sucker up as soon as it started leaking I imagine. Must have been the wrong felt seal.. the old one was tiny.. only about 1/4 inch thick. and not compact like it was crushed to that size. It also had a rubber face on it. The new one was about 3/4 inch thick. Some of it splayed out when I tightened the front down.. Hopefully it was only on the front.. or I'll have the same problem again potentially.
The output shaft has a slight groove where the seal rubbed.. palpable but not visible. Should be fine for my purposes. New one fits snugly.