$1000 a month? No. I could not make it in any way that was not squalor, boredom, and continuous financial insecurity. I like going places and doing things. I like knowing that I have plenty of $ for emergencies and that I can afford to go back to S&B any time, that l live in a metal box with minimal material goods because I choose to do so, not because I am forced to do so. That makes a difference in how I react to the inevitable annoyances.
You already got some good info on Medicare. In our case, they take about $150 each out of our monthly checks. Medicare premiums will have to rise in the future to keep the program solvent. You will also need some sort of supplemental insurance to cover what Medicare does not. Ours is currently free as a result of a union contract. But yours will probably not be free. I don't know what others are paying. As you age, you will use it. Don't forget dental care, which Medicare will not cover.
We are steadily losing free parking, especially in urban areas. That means you have to figure some sort of rent and/or fees into your plans. The further out you have to go, the more fuel will cost you. Also, you can't always choose where you want to be. There are a number of YouTube nomads who have found themselves forced into extended stays in places they don't want to be in order to get themselves or loved ones thru serious medical issues.
Re a job. It Sounds like you as not working, now, and are living of you EBay trading. So, get a job. Definitely. Get two! Work until you are 70 if you can. It absolutely will have a serious effect on your SS. SS is calculated on a formula that weights your last year's of work.
Get everything possible done under your employers health and dental plan. Put the maximum into your employer's 401k plan and save the rest. Keep your lifestyle the same as it is, now. Just because you are making money does not mean you have to "reward" yourself by buying a bunch of junk you will have to leave behind, anyway.
Remember your goal. Get out of debt. Save, save, save. Even at minimum wage, you can have at least $100,000 at the end of 10 years if you save your wages and keep your lifestyle at the level it is, now.
Just an aside, don't get your vehicle until close to when you go nomad. Drive a beater or take the bus or whatever you are doing, now. The best way to start out is with a good, reliable vehicle and an extended warranty, about a year before you go fulltime. Even if you can do a lot of your own work, now, you may not be able to do so in your 70's or older. Take trial runs. Lots of extended trial runs. Find out what annoys you and fix it.