There's a ton of good material in there.
I finished cleaning up lower unit, and pressurized it to 10 psi through drain on bottom of unit and plugging top oil hole (where o-ring sits). It held steady at 10psi. For the heck of it I loosened the new shift shaft bearing assembly and it did leak as expected. Lower unit looks great now.
I'm removing the upper unit now
You are figuring out a ton of this on your own, good work. Yes that oil you found on the shift assembly was dripping from the upper, I too had a big gush pour out and was worried a seal in my upper was toast, but I realized it wasn't the case once I started to clean things up.
The pressure test is the sure way to figure out what is leaking. One thing to note,
you already changed out the shift shaft bushing, so that may be why it was leaking and your problem may be solved. The upper may be fine as is, but it doesn't hurt to pressure test it to be sure. I did a pressure test separately on my upper, lower, and then together once they were reassembled. I would say do a pressure test on the upper, if it holds pressure, reassemble and do the test again. Use a bottle with water and some soap mixed in and spray areas of the drive, if a leak is present it will bubble and you can pinpoint it exactly. If you still have the lower separated it might be worthwhile to retest it and spray with soapy water if you didn't in case there is some other leak as well. From what I understand there are more serviceable areas on the lower versus the upper where it requires more tools and skill.
If you ever come across another issue its usually best to do the pressure test first since that will lead you directly to the problem areas. In my case the shift shaft bushing was the culprit and I had the exact same symptoms and experience as you. Hoping it is also your problem and it is solved. If the upper is having leak issues, from what I read it is mostly a seal that cannot be easily changed and requires special tools, basically not a DIY type job. It was my first time breaking open a drive though so others can chime in if you find new issues in the upper.
For reassembly of the outdrive once you have it back together, a member here on the board (@achris) has an awesome video on how to reinstall, check it out:
https://www.youtube.com/watch?v=aGVrY4cWiDA
Give us an update once you get further!