("I am hesitant to disassemble too much more at this point.") <<<<<<I know that feeling, guess you have to come to a decision, am I going to make it worse if I keep going, or am I gonna to find the problem if I do keep going and most important will I remember how it goes back together, check mate would be you have it apart but still know what the problem is, but the tractor still works, just no 3 point lift.
If it does go south, at last resort you can mount a 12v 10,000lb winch with remote on the ropes to lift the 3 point lift, that's what I did 8 years ago to lift my pto winch, mine is a little on the weak side when I have 5-ish- 6-8" trees on it.