When I removed the pan on my 57 292, it took a lot of wiggling etc. to finally get it free. I did a dry run before actually installing it and it slid in, no problem. While reading some posts on the Ford Barn, I read where someone had a hard time getting the pan off of a 55 272. Someone advised that the manual said to make sure that #1 was at TDC. It just happens that my #1 was at TDC when I replaced the pan.
Yes, you have to have the crankshaft positioned so the rear counterweights will not interfere with the oil pan rail during the Re & Re.