727 Transmission issue

Think a about this.
The fluid is thicker when cold allowing less bleed by.
Sounds like you might have some clearance and/or sealing ring issues.
Very first thing I would check is to make sure no valve body bolts loosened up.

There really is no adjusting the shift into third without affecting a bunch of other things.

Other than that you might put a gauge on it and test its operating pressures.
Valve body bolts ? So I guess I will have to drain the fluid out to check this... Thanks