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: "Automatically start Simon when you log in to the ...
Thanks for pointing this out. I confirm that it doesn't seem to stick. I'm not sure why, but will investigate.
In the meantime, a workaround is to choose Open at Login from the Dock menu's Options submenu, or use the OS X option to restore open windows.
Re: "Automatically start Simon when you log in to the ...
Thanks!