I think the problem with that is - if he's already lacking motivation for regular life - going into a dream vacation will just make regular things mundane. He's got a lot of money so he could probably keep up that lifestyle and live off investments ... but have to be careful to not go broke like many suddenly rich people.
Personally, I would be bored as hell after a month at a tropical beach and be very excited to get to work on building something--anything! Maybe that's not what everyone's response would be.
