I think it's the "minimum effort required" barring people from switching. How much they can be complacent and tolerate the bullshit of a hostile OS they are used to.

From a low pressure sales perspective the community should be phrasing it as questions that make the Windows user think about.

Even aside from this, I think the bigger issue is that Linux evangelists need to be open to new/ignorant users, and casual users. So much of the Linux community is made up of die-hards who expect other users to be just as invested in it as they are. For example, I've tried Linux twice, and both times ran into issues with support for hardware (audio issues the first time, lack of support for my mouse the second). In both cases, I have a significant number of people making absurd suggestions, and expecting me to devote significant amounts of work or money to make my PC functional when I already had a functional OS. Comments to the point of, "just buy new hardware," "just program the drivers yourself," or "just hire someone to write the software for you." were a significant part of the response. Unless Linux is my job or my hobby, these are not realisitc suggestions, and they make Linux look like a nerdy hobby rather than a Windows competitor.