Lukie, I think in general your advice is very sound and prudent, but I also think if this guy hates his job, has a tolerant wife making good money and wants to give it a (long) shot, well, more power to him. I've recently started transitioning from working more to working less by way of grinding low-stakes games, and, while I can tell it will be a touch and go way of making a semi-living, it's also a thrilling thing to attempt.