Simon 5 is coming soon!
Simon version 5 is currently in beta testing. It is a massive update, introducing a much-requested feature: syncing the Simon data between multiple Macs, plus a Simon Status service, a Link Checker filter, improved Find filter, iMessage and Speak Error notifiers, a new app icon, and much more.
Important: please note that Simon 5 requires a minimum of macOS 10.12 (Sierra), and will be a paid upgrade from Simon 4 after the beta. Purchasers since September 1, 2020 automatically get a version 5 license (that also works in previous versions).
Re: Reboot
Yes and no: Simon doesn't have direct PowerKey Pro support yet, but it works via AppleScript, and Simon can run AppleScripts (saved as applications) via the Launch notifier, so Simon can restart a PowerKey Pro via that mechanism.
Other reboot options
I've used Whistle Blower as a monitoring tool for many years, and am largely happy with it. WB not only monitors systems, but after a user-defined period of contact failures, WB can be programmed to use the SSH, Telnet or web interface of the APC products to log in and trigger a power reset of individual outlets. Nice for automated resets. However, I've had to move beyond APC Masterswitch 9606/9211 devices to the AP7900 series -- and Whistle Blower development has apparently stopped.
I'll download Simon and check out undocumented features to see what it can do, but I do not see a way to program an 'action' that would allow me to log into the masterswitch admin, trigger an outlet reset, and await results. Am I overlooking anything here?
Re: Other reboot options
You can use the Launch notifier to start an AppleScript saved as an application, which can do whatever you require.
In the next version of Simon I plan to extend the Script service to a notifier too, which will be even more flexible in what you can do.