This thread hits home for us 'cause we're all cowboys at heart. I'm 56 and putting things in place for similar reasons. How I pay for it??? First I have two rentals bringing in 1400 a month clear, I worked 25 years to acheive that. My ex is got the others and is trying for these. So no guarantees- I could still lose it all. I decided to start living in a rv as a base camp. 1 year now or two? I have no retirement, wasn't offered at work, and ex appropiated all our savings, again years of work with no reward. I did get about 40% of assets so I do have value there. Start traveling now?? Big yes in my boat! How do I pay for health insurance?? the major unknown, I can always get a low-end short time job to supplement rental income. But not health care. At this point I looking at being non-insured till Obama catches me!