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What’s a watch to do things like this that might not have this many hoops to jump through?

The new Pebbles, probably. They have very nice hardware, long battery life with always-on screen, open software, and an active developer community.

Not the same target groups though, Pebbles is C and JS, whereas Pine64 is C++ and MicroPython.

Would love to see wifi support

I moved from PineTime to https://banglejs.com/ Price about the same but the tools IMHO was easier.