One of the tricks I learned was to purchase the pan gaskets for say a 216 and then also purchase a set of pan gaskets for a 1962 235. The late model 235 rail gaskets wont work on the 216 but the 1962 235 end gaskets will and theyre rubber, not cork, and lot easier to work with. I also use a THICK chassis grease for holding the gaskets in place with a little bit of Silcone on the corners where the gaskets "meet".
Other than that it just takes some of us a little frustration and a few sets of pan gaskets to get the knack for installing a pan from under the vehicle.
Good Luck! Youll get the knack if your stubborn enough.....