STRETCH QUESTION: 1986 SS 18K Datejust Jubilee

[ajoh]

Hi - My wife's 1986 SS 18K Rolex Datejust has recently been serviced by Rolex. They did a wonderful job. The Jubilee bracelet has minimal stretch for it's age. I have a couple of questions:

1. I purchased for her a Wolf watch winder as she alternates watches. The accompanying pillow was much too thick, so I ordered the small pillow. The small pillow is better, but when the watch is placed on the pillow it is tight and the watch doesn't move at all - basically you couldn't insert even a pencil under the band. So, will this tightness on the pillow cause additional bracelet stretch? Should I be looking for a different option as she has such a small wrist?

2. When the watch came back, there were instructions to manually wind it for 30 - 40 times. We did that. It is safe to keep it on the winder, which alternates directions and rests periodically (900 times per day, I think), all the time when not worn - or will this potentially damage the mainspring even though Rolex builds in protection for overwinding?

Sorry this is so long, but servicing and bracelets are very expensive and just want to make the watch and service go as far as possible.

Thank you to everyone!