AMA: Troubleshoot device issues with Intune

1. previously when we do a fresh start to let another staff member to enroll via the autopilot once again (since we can't change the enrolled user and give them admin level) instantly. I believe that machines membership does not get removed. So on a fresh start shouldn't it remove the group memberships of that machine when someone signs into the redeployed machine they do not have those memberships intact. Are we missing a procedure in re-deploying machines to other staff members? 2. when they do a fresh start can we specify to have it download the latest version of the Windows OS?