Those with issues, can they ping (fqdn / ip) and resolve the server ok? Do they have a valid IP, Gateway and DNS address?
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What happens when you actually try to connect, let's say with cord?

Right-click on Microsoft Remote Desktop in the tray and select Options Keep in Dock. Click the Microsoft Remote Desktop window. For Microsoft Remote Desktop 10, in the menu bar, select Connections. Microsoft Remote Desktop (RDP) for Mac is a useful way to work with Windows apps and resources. Even though you’re operating macOS, you can still access PC-style desktops from your MacBook, iMac, or Mac Mini. You can use RDP for Mac on any computer using macOS 10.10 or newer. Jan 07, 2020 I just tried my MacBook Pro and it connects. So, I believe it's something with the newest Mac OS Catalina update and Remote Desktop 10. Below are the credentials: MacBook Pro (which works): Mac OS High Sierra v 10.13.6. Microsoft Remote Desktop v 10.3.3. IMac (which does NOT work): Mac OS Catalina v 10.15. Microsoft Remote Desktop v 10.3.3. Microsoft Remote Desktop (Formally Known as Remote Desktop Connection) in MacOS. Microsoft Remote Desktop, a free application from Microsoft, allows you to use a Mac laptop or desktop to connect to and work from a Windows desktop computer that you have RDP access to in your on-campus office or lab. Download the Microsoft Remote Desktop client from the Mac App Store. Configura il PC per accettare le connessioni remote. Set up your PC to accept remote connections. Se ignori questo passaggio, non puoi connetterti al PC. (If you skip this step, you can't connect to your PC.) Aggiungi una connessione Desktop remoto o una risorsa remota. Add a Remote Desktop connection or a remote resource.
Can you telnet to the server on port 3389 ?
There should be no need to install a cert, it might prompt you to 'accept' or 'verify' the server and that should be it.

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Can they connect ok when they are on the same network?
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Have you tried to give the MAC a different IP so you know it's not a conflict?+
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You might have routing issues with them being in the same subnet...
