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I've noticed the same "Approaching Schedule Limits" message. As you noted, it isn't consistent. For example, it came up today as I was trying to pause a user with 12 devices assigned. I was able to work around it by reassigning most of the devices to a different user and then pausing them one at a time.
I agree that the bug is quite annoying and that I'm surprised there isn't more discussion about this. If this limit is real, then it's much too restrictive (I have about 20 devices and 6 users).
This seems to be a rather annoying bug that is not consistent in its presentation or outcome. You can remove bedtime modes or devices and get it to sometimes accept your change, yet still present the vague warning; or sometimes it ignores your changes before posting the vague warning. At the very least the wording is poor since it implies you are approaching a threshold, not that it is dropping the request or part of the request. To get anything to function I tend to start dropping scheduled bedtimes on the older kids to try and get the focused kid's to work and then slowly add the others back until it errors. Sometimes they all seem to work. They used to work for months but no longer do.
In any case this arbitrary limit that seems to come into play for as few as 16-20 devices for four child schedules and two bedtimes each is really low. I can't imagine designing this without support for the number of devices that can be active on an 8-bit subnet at one time. 255 is a much more reasonable design limit. The tested limits must be very very low as compared to the capacity. I'm very surprised to not see more discussion on this.
Millersmom320, I can look into your pausing issues. Please send me a private message with your full name and account associated phone number for help.