Engine oil pan and trans pan both have bad leaks, never changed the gaskets on a small block before, it is a long pain in the ass job? Had a local mechanic said he hated doing them on 318's, which is what I have in a 69 Dart.

No garage at home to do it in so I am thinking of paying a shop to do it.

Any advice?

He means he hated doing the SB in an A body, the trans will b easy for you. Get the good pan gasket at the dealer 4295875AC & a filter & can easily adj the inside band while you are in there but are you sure it's the pan gasket leaking as tranny leaks can b very deceptive & there's several other places (on the trans) it could b.