I have had this issue for some time, but it seems to be becoming more frequent now. Some of my rules stop working randomly, including Basic rules, RM (Legacy) & Simple Automation rules. At the same time, other rules within those apps keep on working. Here is one example of randomness, but I can share more from other apps with similar behavior (or where it didn't fire at all). And yes, it has been colder than 72 in this case and thus I expected it to fire everyday. I am on C7.
I don't see conclusivve evidence for this. What you'd need is a lack of log entries for then app at the expected time (which you should have since I see you have logging enabled in the app). What appears to be a rule problem is often just a device not responding as you expect, and the event history you did show for the device tells you what the device reports back to the hub, often in response to a command, but not what commands were actually sent.
You've got some good advice above that should help you get started figuring that part out. Just wanted to add a little in about troubleshooting in general. Good luck!
Here we go below (I had to redact a few of the names for privacy reasons if you see some device names blurred out). I see a couple of orphan nodes - Wink hub died, it seems, and one of the shade remotes is also MIA physically, so I can't exclude either. I tried to run a repair on both, hoping it would give me a 'remove' button (this approach has worked for me past), but I didn't get the remove option. I guess the next step for me is to force remove it from the device page & wait for it to get removed from Z-Wave Radio after some time?
Your mesh seems a bit weak in places, especially 0x02 (the motor). You could probably benefit from some beaming repeaters... (I reccomend Ring v2's) Even though you have a lot of mains powered stuff, if they're in metal boxes signal can be hampered (as well as plumbing and electrical in the wall)