So, I went ahead and replaced both the oil cooler and the oil housing gaskets. Then, I went ahead and cleaned everything up again. I am convinced that my drain bolt is the source of all that mess in the pics. About a year ago I had my drain hole retapped (don't ask me why , and I think now it's leaking. I applied gasket maker and the leak stopped. The oil pan gasket is leaking too, but it's not nearly as bad as I originally thought.

Now, I have to figure out what to do about the drain plug leak. I think after retapping the bolt goes in a bit at an angle, so the washer doesn't hold well. I am going to try to use two washers next time, if that doesn't work then back to gasket maker. Any other ideas?