The fear of a resume gap is pretty tyrannical, I think a better solution than being afraid of ever going a while without a job would be resolve to just lie if you have to. Plus there's a variety of ways to make money other than a job, not all of which are illegal.
Legit used to have a friend who was like this. He'd always apologize for being an inconvenience - eating my food and opening windows while the AC was on. Like I liked his company and he'd play games with the guys. But after awhile it was like "ok man it's been a year, 3 years, 5 years you need a job you can't just live at home no income" But he wouldn't change anything. No job or friends outside of us. After a few years it hit a point where I couldn't afford it anymore. Roomate and I had a sit down with him, said "alright bud shape up or ship out we can't do this anymore". Hooked up the computer so he could job hunt and left for 2 days. Came back and checked the history - 16 episodes of DBZ watched, 2 jobs applied for. And that was the end of the friendship.