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: Updates on passworded site
Yes, it sure can. There's two ways sites handle logging in: via authentication (where your browser asks for a username and password), or via cookies (where you use a login form on the page). Simon can handle both.
If the site uses authentication, you simply enter the correct username and password in the Security section of the Edit Test window.
If the site uses a form and cookies, you can visit the page in the Preview window and log in while the Edit Test window is open, and it will record your cookies and use that to log in later.