I watch a number of people doing the "vanlife" thing on YouTube. They tend to get burned out after a year or two, and head for terra firma, or they fall off the map indefinitely.
I would not recommend it. A van that you have to furnish will be cold in winter (and no, lots of blankets will not help when you have to get up and ready for work), hot in winter, always vulnerable to meth-heads on one side, as well as the police looking for anyone out of line (and one citation, boot or tow will set you back months to years.)
I don't walk in your shoes, but can you sell or pay off the Sportster? The key is to start getting more cash flow in, so you can start saving, perhaps tossing something like 5% of the income into a 401k or an IRA. I'd also look for online training for something else.
Were I in my 20s, and not making it, I would be taking some high-impact martial art to get the body in shape ASAP, then I would go to a recruiter. The martial art will make the physical part of Basic training more bearable so you can focus on the mental exercises. On the DD-4 form, I'd make -sure- to have some stipulation that you get a TS/SCI clearance on it. Choose your MOS, and hang on for your enlistment term. It will suck and be brutal... but when you hold that DD-214 in your hand on your way out, you can go to the next phase of your life. If you like computers and have a security clearance, there are -tons- of jobs available, even if you don't know that much about stuff in the first place.
