I won't try to disguise myself as an expert, but I'll give you a little of what I have seen as far as leaks are concerned. Seems like the most common oil leak is from the valve covers. A couple of weekends ago, my dad brought his '84 Chevy truck over (350 V-8) for me to take a look at. He had a terrible oil leak. Although he's a motor head from way back, his age and poor health keep him from crawling around trying to track down leaks. I put it up on ramps and crawled under. Oil everywhere!! I'll shorten the story here and just say that after looking things over, I decided to just check the bolts on the valve covers. With all the California smog equipment in the way, that's not an easy task. At any rate, I got to the bolts and was able to take a minimum of 1 1/2 full turns on each of the bolts in order to get them snugged up. The oil leak is gone.
On his transmission, the cooler lines were loose, again leaking fluid. Tightened them up and viola, no more leaks. I've also seen auto trans pans that suffer from being over tightened, which deforms the lip of the pan and squeezes out the gasket causing a leak.
I hope some of this helps you out. I know how frustrating finding fluid leaks can be.