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: automation
No, that isn't really feasible at present. I do have some plans for a future version that might enable such functionality, including command-line access to Simon, but can't say when that might be implemented.
Simon does have a Setup Assistant that will let you import bookmarks en masse, though.
Re: automation
thanks for your reply... The product is great, but without automation, it's a bit useless for me... So I guess I have to keep an eye for the future version...