I would look into node management systems similar to Canonical’s paid “Landscape” service. A quick search suggests open-source alternatives: foreman, Puppet, and Spacewalk. They are designed for managing server nodes, but I suspect managing multiple IoT nodes will benefit from the same system structure.
Update: since Caffe samples are compiled in Python, you could also try Jupyter for each node’s local WebUI. I set that up on my JTX1 yesterday.
Barrett