I don't see tremendous oil on those outside cylinders so much as a fluffy black, so I'm thinking maybe a fuel mix or incomplete combustion. Deposits on the underside tulip of the valves, baked carbon under that surface soot, and carbon on piston tops would tell more of the story for those cylinders. An even better way to spot oil is to read the deposits on the old spark plugs. I suspect Jim was probably idling the engine a lot more than driving it around, so that makes me think vacuum leaks, fouled injector nozzles, or perhaps simply the engine wasn't fully warmed up when it was shut down.
My injectors were super crusty at 50k (likely from sitting so much and cheap gas from south of the border). I had my injectors ultrasonically cleaned and flow match checked. It made a noticeable difference in torque and even gained a about 1-1/2 mpg on my V10. I'm thinking Jim's got a couple of crusty injectors with funky spray patterns and this would tend to reveal at more at idle as a soft misfire in those two holes. The computer trim would tend to compensate more at speed. It's a little pricey, but this is where I sent mine and he had decent turn-around time.
http://www.mrinjector.us/
Hey Jim, a couple things I'll pass along about that engine family. Use only a genuine Motorcraft thermostat (check with Ford for current recommended p/n). The design uses a recirculation/bypass to quickly warm the engine. Aftermarket thermostats just don't work right because the dimensions are off. Also be sure to use the severe-duty thermostatic fan clutch; standard van clutches are super whimpy and won't pull enough air but still bolt up to the fan. This is the one I used, check if it applies to your V8 too.
https://smile.amazon.com/gp/product/B000C3BB3A/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1 Comparing the two you would see an obvious size difference. Check the back of the serpentine tensioner for rust at the clock spring and replace if any red powder is evident.
Thanks for keeping us updated on the progress, great pics too!