This dilemma is an old one, for sure. SLC Punk addressed it to some extent; at a certain point either you have to decide whether you're going to let the lifestyle kill you or turn you insane, or whether you're going to "sell out". Living a wild and free lifestyle has a price, and the older you get the higher that price gets. Your teeth start rotting in your mouth because you don't get proper dental care, your health goes to shit because you can't see a doctor (free clinics are shit and don't count). You get sick of watching your friends die of drinking and overdoses, or lose their mind because they got fed too much acid at a festival. Your dog gets old and can't walk 20 miles in a day anymore, assuming your dog doesn't get a major problem and get put down because you can't afford a vet, or get taken away because you went to jail for too long.
I had to switch to an apartment and a 9-5 after 5 years of traveling + 3 years on a boat + 2 years living out in the woods, and it's definitely a hard transition. My time isn't my own anymore, the lack of freedom is real and painful. Every other week I'm about ready to say "fuck it", get rid of it all, and put the pack on again. The only thing that keeps me going is that I'm doing all this so I can have real freedom, rather than constantly trying to scrape up tiny amounts of cash so I can meet basic needs, and not really being able to see the world because you need money to leave the country. It also makes me feel really good finally getting long-needed dentistry done, and being able to go to a real doctor who actually gives a shit about me (versus a free-clinic nurse who doesn't even look at me).
Either we sell out, or we die from some stupid accident on the road, or we die old and alone of some stupid preventable illness with a mouth full of rotten teeth living in third-world conditions, the way I see it.