Unless it's actively weeping/seeping around that gasket, or it continues to weep/seep after you get the oil down to the correct level, I wouldn't bother changing it. It would look dirty in any event and if the transmission is overfull it may even be seeping. With the oil at the proper level it shouldn't.
For oil, 85 or 90 weight gear oil will be fine. It's sold in larger quantities, but also (lucky for us with small tractors) in quart bottles. You'll find it in almost any brand, Valvoline, Havoline . . . I think Valvoline makes the NAPA labeled brand. It's hard to screw up gear oil, so any rated brand will do just fine. Some guys use a heavier weight to try to quiet down gears whining, but if it gets real cold where you are, the heavier weight might be a little stiff in the winter.
If your transmission were absolutely clean inside, it will hold five quarts. IF it has a PTO on the rear, it will hold an additional half-quart for 5-1/2 total. (No need to fill the PTO separately -- there is a slinger gear that throws transmission oil up to lube the PTO gears, so as long as you run the tractor for a little while at first without the PTO running, it will be lubed just fine).
Because you may have some cake or sludge in the bottom taking up room, you may find that yours will take less than the 5 or 5-1/2 quarts. That would be normal.
Have 5 or, if you have a PTO, six quarts of gear oil on hand when you start. After completely draining, just refill until it comes out the check level hole.
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