@NinjaKun’s great thread about headless server and @StevenCombs’ MAC instructions helped me a great deal back then as I am mainly a headless guy. (That, and the fact that power/brownout, etc., had given me enough frustrations using GUI.) As much as the GUI is fun, I find many capabilities in CHIP great for headless exploits, and would like to encourage broader headless hackers to consider CHIP. The subject of getting into CHIP headlessly traverses multiple OS’ and can easily frustrate a beginner. So I wrote a combined guide last October: Programme the $9 C.H.I.P. Like You Would Arduino. It allows users of MacOS, Linux, and Windows to each follow a straightforward, minimal procedure to get to the command line via serial-USB using a regular USB OTG cable.
(Since then, @Petrakis has updated his thread about Windows composite gadget driver. I’ll need to update the complicated Windows workaround with latest information. Anyone knows if Windows 10 will officially include the “official” driver?)