I am planning on installing a push-up mast and I am wondering what the best way to attach the guywires to the roof is.

The mast is a push-up 30-ft mast attached to the ground and the side of the building in the corner where the building makes an "L" in the picture below:
I will attach two sets of guywires, one set at 20ft and the other one at the top (30ft).
However, I am unsure about what the best way is to attach the guywires to the roof. Do you have any recommendations?
Can I trust some eyebolts? How long do you think they should be? How would you seal the whole? Silicone caulk?
More pictures here: https://photos.app.goo.gl/CDKbVeXSthENVkWX6

Thank you!