59 Cruise-O-Matic on a 352
Questions: What pan gasket is correct?
Should the old filter be cleaned an reused?
How many quarts with the torque converter & with out the torque converter?
Advance auto or Auto Zone probably will have the fluid change kit just bring your old gasket or pan with you so you can compare them, the kit with the filter is under $10 dollars.
When you have the pan off put it on a flat surface and check to see it is completely flat as they usually get a little bent from over tighten the bolts, pound flat if it bent even a little because it will leak if you don't.
Don't use silicone on the gasket if it is a cork gasket as the gasket will squeeze out, if it's cork glue the gasket to pan, you can put a very light coat of silicone on the top of the glued gasket being careful not to get too much on because it might get into the transmission.
The Transmission holds about 11 or 12 quarts 3 or so are in the torque converter, use type F or FA fluid.