If the front seal was leaking, fluid would have to travel to the end / front of the input shaft main bearing retainer to leak out and it would drip down and exit out of the hole in the bottom of the dust pan and onto the ground. The 59 front bearing retainer did not have a weep hole.

I think I would bring the oil level back up to the bottom of the fill plug hole and then recheck the level the next time you drive it and see a "puddle". Unless the rebuilder failed to reinstall the oil slinger on the main bearing (input clutch housing) input shaft, there is no reason for transmission oil to be leaking out of the front of the transmission.

Earlier models 1948 -55 did not have the oil seal , but did have a weep hole at 6 o'clock in the bearing retainer housing to prevent fluid from getting near the clutch plate . What I've read is that the seal was added to address problems with fluid leaking in extreme cases where the truck was being operated in steep downhill grades or truck parked on a downhill grade.

Here's some photo's / illustrations that may be helpful. Feel free to private message me if you wish.
Attachments
SM420 Illustration P1.pdf (212.07 KB, 5 downloads)
Illustration p1
SM420 Illustration P2.pdf (286.86 KB, 3 downloads)
Illustration P2
IMG_5991.jpg (206.4 KB, 75 downloads)
Front bearing retainer
Oil Slinger Input Shaft NOS_zps5owk8ofr.jpg (34.9 KB, 75 downloads)
Pic of oil slinger
IMG_5992.jpg (167.4 KB, 75 downloads)
Input shaft


Ron - - Dusty53
1954 Chevy 3604
In the Gallery Forum
"You can't dance with the Devil and then wonder why you're still in Hell."
"They will forget what you've said, and they will forget what you have done but they will never forget the way you made them feel."