I know this is supposed to work, in theory, but is it recommended to try debian 8 -> devuan ascii upgrade on a remote (ssh) machine?  Will I lose ssh connectivity during the upgrade process, what other things should I be aware of before attempting it?

I don't think you'd lose your SSH connection as even if SSH gets restarted or removed it won't kill your active connection (no guaranties though). Also the last posts in this thread (https://dev1galaxy.org/viewtopic.php?id=2125) might be of interest. Hope this helps at least a little.

Then backed up my "baremetal" system.  Some other errors (depencencies?) partway through, had to run a "apt-get --fix-broken install" then resume the dist-upgrade.  Same issue with wicd, copied system.conf from most recent backup and resumed upgrade.  Rebooted, no gui.  Reinstalled nvidia driver, rebooted, all seems okay.  Remmina was uninstalled.  Opened synaptic to some error, had to run "dpkg --configure -a", now synaptic works.  Had to force specific remmina version (something about backports?), now it is okay.  Had to redo some other minor tweaks, but overall a rather painless experience.  Just kind of curious about that wicd thing, it seems the system.conf is deleted too early in the upgrade process?

I know this is supposed to work, in theory, but is it recommended to try debian 8 -> devuan ascii upgrade on a remote (ssh) machine?  Will I lose ssh connectivity during the upgrade process, what other things should I be aware of before attempting it?

Again, thanks to the developers for their work in this project, and the people who provide forum support / other chat.