Your average person can't build C binaries and benefits enormously from being able to run interpreted languages where they have prior experience, or which are easy to pick up from scratch if they don't. Otherwise the ESP8266/32 boards are useless to them and they're not able to join in the fun.
ESP8266/ESP32 are capable micro controllers which, given their price, are difficult to complete with. That battle might not be worth fighting.
So, looking at software side, strategically, I think you're in the middle of a land-grab. In the long term, is it better that Espruino is the goto solution for coding on ESP8266/32, or that one of the alternatives like MicroPython, Lua or, ESP8266 Basic, has become it?
One could see more opportunity to earn revenue from initiatives like paid support or premium access channels in the above scenario, than if Espruino was used only by folk who bought an official Espruino board, while the ESP crowd ran something else.
Of course, many won't subscribe, and will get more value than they give - as is the case now - but with scale/volume it doesn't matter as much, or feel quite as personal :)
I don't think you even need to understand how to monetise in the short term (providing you can support yourself) if you get the distribution and Espruino becomes a/the standard, these things should fall into place.
If nobody is using Espruino, but the owners of official boards, you don't have quite the same opportunity, if any.