You sound like my kind of guy. I'm a total cheapskate and I run my own company. Health insurance? Ha! Vacations? HA!
Unlike many, I worked hard at low-paying gigs, invested and saved up enough money over about ten years to buy a house flat-out (with some help from my wife's leftover college fund). Over the years I've gone dumpster-diving, gone without air conditioning, eaten lots of rice and beans, not eaten out, paid midwives for home births rather than hospital births, lived with a single vehicle, etc. My wife is a homemaker (praise God) and homeschools the kids, which allows us a lot of flexibility. We also grow a lot of our own food. Obviously, this isn't living "without money," but it's the best way I could figure things out.
All that said... many people are totally buried in debt. If I had made a few more materialist choices (buying the "nice" house instead of the tiny affordable one, going to college on loans, not working extra gigs, etc.), we'd be totally tied to the debt-slave wheel.
If you were to talk with someone in that situation (and I do all the time), what would you say? They're slaves to the banks... slaves to their cars... slaves to their spouses' desires for stuff... ack. It almost seems crazy to say "give up on the money thing," when they're drowning already. They think I'm "lucky" for being out of debt... but they're addicts to stuff and won't make the serious cuts we made to get here. It's frustrating - and I want to help (heck, I've thought about doing financial counseling... and I seem to do it as a layman now) but I feel like it's almost hopeless. I just want to scream "WAKE UP, DANG IT! SHRUG IT OFF! FIGHT!" It hurts to care... but I do care.
I agree with most of what you said except the part about needing health insurance. What will you do if something really tragic happens to yourself or a member of your family. I was diagnosed with Rheumatoid Arthritis a couple years ago and without the insurance my life would be not worth living. Without the health insurance I would not get the expensive medications I need to live a relatively decent life and hopefully not become a complete burdeon on my family or society.
I live well below my means, live very frugally, grow much of my own food, unfortunately do have a mortgage but am paying it off very quickly, but in the event of no health insurance I will soon become unable to do any of the above and at under 60 years old may be totally dependent on someone else to take complete care of me. At least living in the US, it is a necessity to have health insurance unless you don't mind the government telling you what you can and cannot get as far as medical treatment.
Bad stuff can happen, sure. But affording insurance is like jumping over the moon when you have a small income.
I could either be a wage slave at an office and maybe get crummy insurance... or do what I enjoy, go without it and not worry about the "what ifs." There's always a chance - and the system is a wreck - but since I can't afford it, I don't worry. We don't eat gen-mod, we don't eat grains (except on rare occasions), we don't eat processed food... and we just trust that God will keep us safe.
So far, so good.
I'm sorry to hear about your Rheumatoid Arthritis - I have two friends with that. It's a miserable condition - glad you're doing okay so far.