They might get to hang out in the clinic more often, but secondary gain there is limited, because the clinic is full of hard-ass dudes sick with
seriously contagious shit like tuberculosis, hep C and the HIV. Prison med staff get wise to bullshit very rapidly, and are not the cuddly cute woke student nurses a tranny might get in a city ER, because every single patient a prison nurse meets all day every day is actively trying to manipulate them. Prisons are essentially psych wards, and trans people universally shit talk psych wards, probably because they handle personality disorders so often that they can't work any angles on the staff.
Yaniv is really unlikely to hit Canadian prison though. Canada's latest fad is
throwing out criminal cases completely because they take too much time, and Yaniv's whole MO is wasting time. Like
@moocow points out, if he ever gets booked for anything, he'll sit in jail for 24 hours max and be let out on time served.