>The people who explicitly ask for less security get less security.
The problem with that is less security is almost always more usable than more security, which leads to the greater amount of people being in that state, which is not just a danger to the user making the choice, it is a danger to others.
Unless the requirement is extremely onerous, very few people will go into settings to check if it can be circumvented. For homeless people, it seems that it is indeed extremely onerous, so they or those who help them will have a reason to do this, but few others.
Not sure why this is being downvited. You could argue that forcing security upon users is why everyone knows about password-based logon today. Same could be said about the initiative for HTTPS everywhere.