OK I figured most of this this out now. I can successfully configure VGDB’s SSH connections from my automated configuration tool. The only problem I’m still running into is that VGDB only loads SSH connection info at the time when the VS project is opened. So you can open two instances of VS, set up a connection in one, and the other one will not see the connection until you exit and re-open VS. Sometimes it even gets confused and shows the same connection twice, etc.
Also when trying to debug with a valid connection, it would sometimes say there is no such connection even though it is configured in all the right places. It seems ideally it should reload connection info when the SSH connection dialog is opened, and also when starting to debug.
Once again I know my use case is not normal but I can see VGDB getting confused with SSH connections when you have more than one VS instance open, which I think many people do, at least where I work since we work on multiple source code branches at the same time.