I took the Jeep out for a drive.
As I mentioned above, the transmission issues are nearly gone now that there is fresh oil in the deep oil pan.
I took it out on the freeway. At 60mph, the RPMs are about 2300-2400. I probably need a regear at some point.
I'm still having cooling system issues. Around town, it was consistently around 210. When I got on the freeway, it crept up to above 210. It didn't overheat and go into the red, but it definitely get hotter than I would like. Ambient temperature is about 85*. I know there's still a ton of rust in the cooling system, and the coolant/water mix right now is probably close to 30/70. I just really need to do the full cooling system flush again and then see how the operates.
I just drove it around for 40 minutes just to drive around because it is fun to drive and puts a smile on my face. Top down, doors off of course.