Thanks for the reply. This did resolve one of my issues.
Initially I was running the connection test from my workstation, tried it from the server and found that there was no reverse dns configured for our vpn network. Fixed that and now all is green in the connection test from the server.
We are still getting the...
Unexpected failure while connecting to Asset. Object reference not set to an instance of an object.
So I began to attempt the next suggestions of trying to run the command on the client with the exact path, and found that perhaps now it's a matter of connection speed. The error on the client command is 'XYZ.exe is not a valid Win32 application' which indicates the file is not getting downloaded completely (according to a quick Lougle search). I don't believe there is an issue with the command in the package because it works fine on LAN Networks.
The reason I suspect a connection speed issue is because I've been testing on an LTE hotspot and I don't trust the service provider in this area, 400+ ms on most pings... More testing, hopefully will give me a definitive answer. Thanks again, I'll update when I get a better connection for testing.