Hi Peter,
I am pretty familiar with most aspects of Stellarmate (KStars/EKOS/indi). It is now a pretty mature platform and lots of information and help on line. For specific info and help I would sign in on the indilib forum and post any questions there. Answers will come thick and fast.
In terms of going headless from a RPi4. I use Ubuntu 20.04 and Ubuntu Mate as the desktop and the process was seamless. I also find NoMachine (free) a really stable way to dial in and control the Pi remotely.
PM me if you are having problems and I can guide you through the process.
Use the stable versions and resist the temptation to update with nightly builds. These are designed for testing new developments but can also cause unexpected crashes.
Mike
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