Good news!
Today I got a lot done. I went to AutoZone to get new hoses and hose clamps for the leaky fuel deal. Terry, the guy who always gives me the wrong shit, gave me the wrong shit. I take it back up there and they do an even trade for the right hoses (4x more a foot. i.e. $8 a foot, I need four). So I got $24 worth of hoses for $4.
While I had the car properly jacked up, I took a closer look at the tranny. Turns out that the dips I was seeing coming from under the car and the wet looking residue near the tranny was from the gas issue, not the tranny! The tranny just had some grease covered in dirt on it, giving it a brown/redish appearance. I wiped the grease off and it hasn't been leaking at all. I even stuck my finger in the bolt holes and poked around, no tranny fluid!!!!!
Things are looking up!
Note to self: diagnose the problem when the car is fully jacked up, not when you have 0.5" for your nose to turn under the car.
Also, expect a automatic tranny fluid change DIY in the future.