You give one example of how the devs (who, of course, fully 'get' Linux and are fully bought in to the experience) have seemingly little insight into how this impacts less able users. (Somehow they think that creating ssh and wpa_supplicant.conf files in the boot folder are less confusing then an extra option in the installer!?)
Other examples (from my very recent experience) include simply trying to install fairly mainstream libraries on a Pi: it took (literally) several days, multiple retries, multiple failed approaches from blogs or stackoverflow, before I could get a working install of python-opencv. (And my final 'success' was just sheer luck, plus trial-and-error, I think).
And there are other examples; every time I start a new project thinking the Pi is the perfect starting-point, the ultimate time taken is 5-10x what it probably should have been.
If the user experience is this bad for someone with otherwise strong IT ability, how on earth do they expect anyone with less expertise to succeed?