Complete re-edit. Trying to rephrase my question, based on some good comments. Made several questions in the hopes that they combined paint the picture and that atleast one of them is understood :)
Q1: For an object in free fall towards a mass, will time gradually slow down for the object as the object gains velocity towards the mass and as the object gets nearer the mass, relative to a stationary observer?
Q2: If we have two identical clocks, one stationary in flat spacetime and one in free fall towards a mass, will there by any difference in the passing of time between the two clocks, relative to a stationary observer? (I guess that GR tells us that both the gained velocity for the free falling clock as well as the lower gravitational potential both slows down time for the free falling clock, relative to a stationary observer - but my intuition tells me that experienced time for the two clocks will be identical . i.e. that the two clocks runs synchronous while one is stationary in flat spacetime and one is free falling, but only while its free falling.)
Q3: If the answer for Q2 is yes, then has this been experimentally verified - how was this done? How would it be done? We know that time passes more slowly at the surface of the earth than at the peek of a mountain and this has been experimentally verified. How do we measure the passing of time of a free falling clock relative to say a stationary observer on earth?
Q4: If we consider a single clock at rest relative to a large mass (carried in-air by a still butterfly), when the clock is released by its tender captivator and starts a free fall will its time slow down / be unchanged / speed up relative to the time of the same clock while it was at rest?
Q5: If we have two persons of the same measurable human age, one staying stationary in flat spacetime and the other could somehow be put in free fall toward some mass for a long time measured by the stationary human. Then the stationary human has a magic wand and creates a worm-hole which allows the human who has been free falling towards some mass (in a more and more curved spacetime, with greater and greater velocity toward that mass) to instantly step through the worm-hole and stand next to the stationary human again (a non-ageing worm-hole!). How would the free falling human have aged compared to the stationary human?