3) After setting up your schedule, a Force Update must be sent to the player to download and write the schedule on the player. Please see: How Do I Force Update Players
The time range needs to span 24 hours for any scheduling to work correctly. For example: First asset could be 12:00am – 1:00pm, next asset would be 1:00pm to 11:59pm. Please also ensure that the time is set correctly on your player.