So then…
I have 2 endpoint devices that I need to run and debug simultaneously. They are on two different IP addresses: 192.168.1.22 and 192.168.1.79. However, the debugger can only specify one of them at a time.
How do I resolve this problem?
two PCs 
Run a virtual machine
yes, this is even better
OMG. Guys that would mean 3 VMs for 4 targets in total. Tis a lot!
You can try VSCode
We’re not doing VSCode.
So you guys are storing the setting under c:\users$name.endpoint ?
Even when I created a new environment for Visual Studio, it used the same encrypted connections.json for all of them. This is hardcore, my dudes. Multiple machines are needed to debug multiple endpoint devices. Deep Sigh.
yes, so it is hard to have multiple device at the same time for now.
We may add this feature in the future.
what if you setup another user account and remote desktop into it?
That would require server OS. And they only give you 2. I’m stuck with making multiple VMs. So I’ll have to be smart about it. I think I can get away with just 1 extra VM for the time being.
Just Windows Pro
So, the GHI stuff in VSCode is wrappers around shell commands, scripts, and executables (like the debugger) that you also have direct access to. While it’s not as slick as just pushing F5, and while the GHI extensions could be improved to make it F5-easy, you’re not blocked from creating a tasks.json/launch.json that does the right things to set up a debug session in a way that allows you to launch two or more instances of vscode for parallel debugging.
For myself, instead of investing in VMs and computing iron, I would probably invest on learning how to launch remote debug sessions in launch.json and then launch two or more vscode instances on your desktop.
(and fwiw, supporting parallel debugging of multiple targets is kind of an edge case, so I don’t fault GHI for not investing in it. That’s also not well supported by jlink, stlink, eclipse, stcubemx, etc.) They all require some extra plumbing or hardware, but also in most of those cases, it’s still doable.)
And that’s why I love Visual Studio Community Edition. No limits.