JOHN POWELL FTW!
If it wasnt for the pics you sent i probably wouldn't have figured it out..
i didn't have that little o-ring/gasket on all the way into the groove.
what it appears was happening was that since it wasnt in the groove, it could float around in the elbow. pumping the clutch pushed it down enough to create a temporary seal, but while sitting or cruising the pressure in the TOB would push the o-ring back up, relieving all pressure and dripping the fluid down into the bellhousing.
time will tell if that's all the issue was. went for a 15 min drive on my lunch break though and everything felt great.