I have some new theories to test. First, did I really see the same service try to start twice. Same names, but were they really the same files.
My favorite theory is this: The connection to port 4448 does not happen immediately as originally thought. When I restarted things to get the connection, the connection was not closed when I restarted my machine. There was no command to my router to close the connection, which created the illusion that the connection starts immediately. When the connection in the router timed out, that's when my problem begins.