All I can think of offhand is there is a person who did something (somewhat) like that in 2015, although not to try and live there but because he said he just wanted to see DPRK for himself and he also hoped he could do something to improve inter-Korean relations, though he was "not sure" how. He was born in south Korea and moved to the US as a child. At age 21 is when he snuck in to DPRK via China. He was arrested (as he expected) and held in custody in what he called very comfortable conditions, and he got taken around to museums, schools, orphanages, hospitals and such to learn about them. He did some press conferences about his experience where he expressed gratitude to the leadership and for being able to learn about the country (here's a CNN report with a video interview of him where he says he's been treated very well) and then DPRK released him to south Korea. Edit: Also, I tried to check for follow-up information about him, but I'm having trouble finding anything.