I feel like a lot of greytiders would pick this just to interfere with security.
During busy chaotic rounds having people whose sole purpose is to be a prisoner who security has to babysit would be pretty draining on security I imagine, and would have them have less energy and resources for antagonists and other crew members breaking the law.
Example:
I see the potential for good RP there and I'm sure there are some people who would genuinely do that, but as it is now I am fairly confident there would be a lot more greytiding rather than RP.
In slow rounds it could work - and would be quite fun - but other than that, it's more or less a powersink on security resources.