This actually is only an issue when a skip occurs, it gets a little tricky! Basically, when you create a fixed or flex monthly schedule, the weather checks all occur an hour before the schedule run time. If on schedule gets skipped, it will inadvertently prevent the other schedules scheduled at the same time from being sent to your controller, regardless of if they are going to skip or not. Hopefully you are not running into this issue any longer after changing the start times to an hour apart.
@mkbattina, are you receiving updates saying your schedule is not going to run? Do you have multiple schedules with the same start time?