I've been playing a little with the pyflipdot library recently to interface with a 20x14 flipdot display, which also uses RS485
Your flipdot display looks like it has a higher dpi, I guess there must be different diameter flipdots made.
The only thing it doesn't have is a RTC, so I just polled a time server every so often.
The battery life on Watchy leaves a lot to be desired, as does the lack of a water-resistant sealed case, but the full featured hardware is a real contender.
The Bangle.js 2 is my second choice in the line up of open source smartwatches.
or (round face!):
https://au.banggood.com/Open-Smartwatch-Light-V3_3plus-ESP32...
With Tidbyt our default pipeline uses our cloud, but the hardware is fully unlocked for you to flash your own firmware.
I feel like for all these connected hardware products, they should ship with an open source server and the phone apps that control them should have an "Server IP address" field in their iOS settings. Your company goes under? I just run your software locally and point my app to my local IP.