I'm not sure it makes a huge difference, but I've read you are less likely to mess up the keyless if you press the stem release button in the winding position for Rolex 3xxx movements. And in most of the videos I've seen of professionals servicing Rolex movements, you almost always see the movement ticking away...so presumably most pros press the button in the winding position. Personally, I have 3 VS3235s and have removed the stems from all of them in the winding position without issue.
and how do you reinserted the winding stem ? (same position)
Tomze