your message shows obvious signs of tractor newby-ism.
a yanmar 1500 is a pretty old tractor. whether the proofmeter is correct or not.. even if that seal only has 90 work hours on it ( doubtfull ), it's still likely old.
Couple that witht he fact that it may have had a clutch job before.. and if so, the seal may not seal 100% perfectly to hold a full sump of oil. Nominal oil level in a tranny is usually LOWER than the input shaft seal, and the seal pust prevents splash and elevation change casual leaks. filling her to the top and expecting a 70's tractor to hold oil is myopic thinking.
also.. as I mentioned.. there is usually a bellhousing drain.. id check to see if yours is plugged.
why didn't it leak earlier? it MAY have, and just took a while to FILL UP the cavity and then run out a non sealed area like starter mounting.
Could you get very lucky and open the bellhousing drain, drain out a couple quarts oil, remove starter and hose the bellhousing and clutch down with a couple cans of brake cleaner, and then adjust oil level in trans to nominal, and maybee it won't be an issue?
Maybee... maybee not.
The correct fix is as I previously detailed.