upgrading older robots

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I have a general question for the community. I have the Deep Learning Robot from Autonomous, a Turtlebot 2-style robot built on a Kabuki base with an NVidia Jetson TK1 for the brain. It came with Ubuntu 14 and ROS Indigo years ago. Unfortunately, as far as I can tell, there's no easy upgrade for the TK1 to later Ubuntus (I have seen some instructions for 16, although there seem to be issues).

• What is the general feeling on the best way to continue to use the hardware?
• Run a VM with Ubuntu 14 and ROS indigo as the workstation.
• Use the latest version of ROS on a workstation, and hope that all goes well communicating with Indigo.
• Something else?

I also have a Rhoeby Hexapod that dropped with Ubuntu 16 and Kinetic. It runs on a Pi, so an upgrade is certainly possible, but I worry about losing capabilities if all the drivers don't have updates.

So, the general question is, how do you all handle older robots?