I have a 102 with a creeper gear. I have had both of your possible problems. The broken driveshaft pin in mine still had the ends out both sides so I just knew this was not the problem but it was. I did manage to pull one of the ends out by clamping a vise grip on it and tapping that with a really long punch. I have made punches from axles out of kids wheeled toys. I now have a whole tray full of punches and chisels. Once I got the one end out I could then align the pin piece in the shaft with the hole where I pulled the end out and managed to punch the whole thing out.
I have had several experiences with the yoke pin falling out. When I removed the little plug on the bottom of the creeper the pin was sitting on top of the plug. I did once replace this pin with the creeper in the tractor but had to issue hearing protection to all the neighborhood kids to protect their innocence. Plus it came out a couple months later. This time I removed the creeper. It is no easy task but by twisting and turning it I got it out and back in the tractor. As I recall when my pin dropped out the lever just flopped back and forth very freely. If yours feels like it is engaging then this may not be your problem.
Since you say you have a seal leaking I would suggest removing the creeper unit and fixing that too.
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With my son, EricR Super 2084 with 54" mower, 451 blower. 2086 with 3 pt hitch, 54 inch deck, 551 blower, 54 in brinly blade. A 4 digit original w deck. A 70 with deck. 2 102s both with 42 in decks, one with creeper, 1 36 inch IH snow thrower CW36, 1 42 inch IH blade. 149 with mower. 2072 w 3 pt hitch, Johnny bucket, 60 in mower, 451 blower. Jacobson GT 10 with mower. DR Lawn vac tow behind,Home made lawn roller. Brinly cart, 2 off brand carts and 1 home made cart.
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