I did not have any issue when i changed out my oil pan gaskets last summer. It had leaked oil ever since i got the truck so i pulled the pan and found the rear portion on the gasket was folded over slightly causing my leak I cleaned the surfaces and used a little permatex to hold the 4 piece gasket in place. Gotta give it time to set up though. And if you don't have one in there now it's good practice to throw a strong magnet into the bottom of the pan to help grab any particulates floating around in the oil system.

As for reassembly, it wasn't too ignorant getting it back in place. I had the front of the truck jacked up and on stands so i had enough clearance to get my body under the pan so i could hold the pan up in place with my chest and one hand while the other hand was getting bolts started. Just be mindful of the gaskets as you get it back in place.