Well, I discovered the problem and Sbooster confirmed. I have an early production Sbooster mk2 that came with an unreliable USB B connector design. They have since remedied this with a new version USB B connector, which is what most people have. As it took a lot of time and troubleshooting here’s the skinny:
The old, original, USB B connector was a 2-piece affair. It uses a 5v pin connector to male barrel connector. Once this is connected to the main unit (with the pins), one piggybacks the USB’s female barrel connector onto the 5v male connector. This double connector design is the problem. With a lot of fiddling I could get it to work intermittently.

The new USB B connector goes straight from 2 pins to micro USB! Much simpler! I expect it will work without issue (once I receive it).
This is probably a weird and rare case, but hopefully this info is helpful to others.