I think I'd have to disagree with most of this.
Homeless teen (trans at that) would cause major problems. 18yo...other than the echo chamber crowd of Reddit, or perhaps conservative Americans (because for some reason, Americans are obessed with a woman's age when she dates for some reason and infantilising a legal adult) no one would give a shit. Look at Dicaprio as a prime example. Villified on the likes of Reddit...in the real world..no one really cares and most men just think, good for you..lucky bastard and obviously, the women themselves don't care either.. Most of the world has no issue with Age Gap dating.
Married woman? Again...it would blow over quicker than the paparazzi could snap a photo of Taylor Swift walking into a dollar store. No would care, except again, the same minority crowd...and the woman's husband (for..well, obvious reasons lol). Rich people get away with all sorts of morally grey shit (I say morals, because there is nothing illegal with an older guy dating an 18yo, there is nothing illegal about adultary, no matter how one feels about it)...they do it every day..the world moves on...people forget/stop caring.
Mason, however, because of the world we live in...would cause him major, major issues, I can imagine.