While I agree that MathJax makes things convenient and far more readable, it seems unfair to demand fresh new users to learn it before posting a question, which is something of a common occurence here. A lot of these questions usually recieve quick downvotes and are sometimes closed. I wonder, if beginning undergraduates or some of the many high schoolers on the site are not intimidated by the barrage of symbols and formatting lessons that go along with learning MathJax as so many experienced users ask them to.
Perhaps we can make a stronger requirement to use MathJax for users who have asked more than a certain threshold (say, 5?) of questions composed of handwritten stuff or images. Should they be readable to at least some degree, one could flag these questions as suboptimal (a new type of flag?) and more than 5 such flags could result in bans and harsher bans on a repeat of this. What this does according to me is to give new users enough time to get around to familiarise themselves with MathJax while also giving them room to ask any pressing queries keeping them awake at night.
For those who prefer seeing uber-readable questions who will downvote a slightly more difficult to read one without a second thought, this can also be a good system to simply avoid such questions by flagging them as such. However, questions under this flag should still be open for answers, albeit filterable for those who get ticked off by issues with readability. Would this be a reasonable thing to do and is it possible?