So I disabled FileVault, let my HDD decrypt, and now I can login from Screen Share/network! So what's my most reliable solution? The machines are in the same room, and I'd prefer to run the mini 24/7.

VNC viewer: Seems to work well, but I'm relying on a connection to their servers in order for the interface to work, and it doesn't survive a reboot, either.

Even if I get it back working again, I'm nervous that every new macOS update will break this.

A recent update to the Duet Display Mac app (2.3.1) seems to crash it every time I try to change resolutions. This used to work very well, as Screen Sharing would display a crystal clear 4:3 interface because it recognizes the native resolution of the iPad. Duet Display w/iPad and native Mac Screen Sharing app with an iPad 5.I've tried using standard network connection, as well as an ad-hoc network with TB3-TB2 direct connection between iMac and mini. Native Mac Screen Sharing app: This works decent, but resolution is not great and it doesn't survive a reboot.fit-Headless: this works OK but obviously it's impossible to connect after a reboot, unless you have auto-login enabled Over the years, I've yet to find a very reliable interface to this machine running headless, especially after reboots.

I like to interface to it via the iMac Pro.

Although my daily driver is an iMac Pro, I have a Late 2014 mini (i5, 8GB RAM, 1TB Fusion) that I run various server-type functions (Plex) via headless implementation.

Ipad to mac mini screen sharing