DST411 is retentive. The others are not.
When the Ethernet was not responding, did you notice whether the Eth LED was indicating a link and activity?
Next thing I am going to want is a Wireshark trace when things aren't happy. Run it from the programming PC, while attempting to connect with DmD.
This one's a bit odd, but comms aren't magic. It's like a small engine...air + gas + fire = run. If packets are getting there, we are processing them, sending responses, and packets are getting back to DmD, comm should work. If comm isn't working, that pathway is breaking down somewhere, and we will find it. May end up needing to do some diagnostic firmware that lets us get more info while failed. It will be important to have USB or serial programming working to get access...ECOM100 could work too, if you have one lying around.
Please send an email to support@hosteng.com with your contact info. That will be better than trying to use the forum.