Thank for the suggestions Tim. Setting the separate ports didn’t do anything on it’s own, but after adding
42177 = email@example.com:4569/42177,NONE to dad’s rpt.conf and
42329 = firstname.lastname@example.org:4570/42329,NONE to my rpt.conf I was able to connect 42329 > 42177… but not the other way around… Some progress is better than none, I am satisfied for now.
Concerned as to why the same settings were not producing the same results on both servers concerns me a bit though and What should I do if I don’t have backend access to the next random node I am trying to connect to?
For now though, good enough. I can just run a remote shh command to his node if I need to be the node initiating the connection because I know the guy and he trusts me.