Well *that* was fun!
Transmission fluid was very dark brown, definitely due for a change. We let the Jeep sit overnight, so the torque converter and cooler also partially drained - better to get as much out as possible. Pulled the valve body and solenoid pack, and replaced the solenoid pack with the modern improved design (the black electrical connector indicates the old failure-prone design; the newer version has a white connector). For fun, we also opened up the old solenoid pack!
New filters, pan gasket, and 8 quarts of transmission fluid rounded everything off. We actually need a bit more fluid, about another 1-1.5 quarts, but I felt comfortable taking it for a test drive. Shifts are noticeably crisper and there's no longer hesitation, so that's good! Bled the brakes again too and the pedal feel is *much* better.
We just need to replace the heater core hose clamps and the center console, and I can start daily driving this!