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: Monitor Windows 200 server Application
If you can SSH or telnet into the machine, like you can on a Unix-based machine, then yes. You can use the Port service to connect to a specific port on the machine, or a Script service to access a program on the machine. Otherwise, I'm not sure; I'm not familiar with Windows 2000.
Can any other readers offer advice?