The pan which covers the bottom of the flywheel has a hole I guess for obvious reasons, to let oil drip out. If it is a quarter size drip after each ride you probably can live with it. Way back when these cars and trucks were on the showroom floor they had "GM Authorized" cardboard mats sitting under the engines to catch drips.
Some people and manuals suggest that after removing the rear main cap you might want to loosen the others so the crankshaft will drop a bit. This is supposed to make getting the upper half of the seal easier to remove. I did not have to do that, thankfully. As mentioned my old neoprene seal came out and the new one went in very easily because they had dried out. The whole job from the time the pan came off until I was ready to reinstall the pan was less than 30 minutes. I had more difficulty getting the oil pan to seal.
While you have the pan off how is the seal and gasket at the timing gear cover?
Bill