Seeing new posts on this thread, I wanted to give an update to my issue with MM, just to let everyone know what my resolution was, in case it helps.
So, in my last post, I created an RM 4 rule to take the place of MM to see if it might help further diagnosing the issue. It actually did because the issue with it not switching into Early-Weekday mode persisted with the RM 4 rule.
@bravenel mentioned:
It being said they are different, led me to look elsewhere in Hubitat for the issue. Looking at the System Events log, I found that the hub was repeatedly rebooting at around 4:50-51 am, which was when my Early-Weekday mode was set to activate. To see if this was the issue, I changed the Early-Weekday time trigger to 4:45 am and, voila, there was no issue switching modes over the next few days.
But the hub continued to reboot, both with systemStart entries for 4:51 am and at random during other days and times. The hub had been randomly rebooting since day one, which I thought was normal behavior. Thinking it was an occasional crash, patch, or some other issue that triggered the hub to restart.
It wasn’t until I found a post from another user that was experiencing the same thing that it was not normally behavior to randomly reboot. In that post, they eventually discovered that the USB power supply was faulty and, with a replacement, resolved the rebooting issue.
I had just bought another Hubitat hub during the August sale for use at a different property and decided to swap out the power supplies and USB cables. And, like the other post, my reboot issue went way. I’ve ran the hub for about a month now and switched back to using MM, disabling my RM 4 rule. I haven't had an issue switching modes since.
As I said, this resolved my issue, but it might be worth looking outside of MM for further troubleshooting.