A few recommendations:
It looks like your “Big Trees, Trellis and Bushes by neighbors” schedule is inadvertently skipping your flex schedule. I would disable climate skip on that schedule. Your flex schedule will then run properly. Edit schedule --> Weather Intelligence --> Disable climate skip. Since you are running that schedule almost every day, we think the soil moisture is full, which is why climate skip wants to keep skipping. Currently if two schedules run close together, and one skips, the other could get inadvertently skipped as well. We will be modifying this functionality in the future.
It looks like your chosen weather station does not report precipitation. You might want to try choosing a different airport, or selecting a personal weather station.
Hope this helps.