I always hated undercover boss because of the temporary nature of the arrangement. Anybody can live on rice and beans for a week if they have to, it's the knowing that it will end and you can go back to your opulence that makes it bearable. They really need to experience no hope to get the real picture. The weight on your conscience 24/7 knowing that it will never get better is what crushes people.
Alternately, give him the entirety of the Moon, with the caveat that the space suit responsible for keeping him alive must be directly and 100% designed personally by Elon musk.
And also as net neutrality is gutted and the oligarchs ensure internet fast and slow lanes.