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: Udpate
I've been very busy on Profile, but plan to do a maintenance release of Simon in a week or two, to add Gatekeeper support, and one or two other tweaks.
I do have big plans for future versions, but don't have a schedule for them yet; Profile and Time Out 2 are more urgent. Simon is a mature and feature-rich app, so doesn't need frequent updates, though I do have lots of ideas for enhancements. And it remains my flagship product.
I don't currently have any plans for reporting changes, though certainly am willing to consider suggestions. For emailing reports, you could use email notifiers to send a link to the report when something interesting happens.
Groups is definitely something planned for a future version... but again, I can't say how soon.
Thanks for the feedback, and continued support.