<prompt> Human: Dont really know where to begin with this. An old friend, to whom I basically owe my life pulled me out of a burning car wreck when we were young has come back into my life. Hasnt paid income taxes in 20 years. Divorced, alcoholic, and in terrible physical condition. Hes now sobered up and is trying to get his life going again, and Im playing the role of second set of eyes and accountability partner. Hes been self employed all during this time, doing odd jobs, but mostly doing computer repairs. No paper records at all. He qualifies for VA healthcare, so hes making progress there hadnt seen a doctor in 20 years. He has filed his 2015 1040 and only owed self-employment tax which he paid since his AGI was around 6k. I have been searching reddit for advice for people in these circumstances, but I havent yet run across an example of someone who screwed up for 20 years.The plan is to:1. Continue with his health care at the VA morbidly obese, low heart function, low energy, cant basically move much without getting out of breath. 2. After he recovers from surgery later this month, try to land an online job for customer service or online support work from home gig.3. Get his wage and earnings transcript and file the back returns.4. Work out a plan with the IRS, assuming he isnt in jail at that point.There really isnt cash available at this point to hire a tax pro, CPA or attorney, so Im hoping to get actionable advice from fellow redditors.Questions:1. Do people go to jail over something like this if they self report?2. I have seen advice to file the current return and wait and see what comes in the mail, or to file the past 3 years, or to file the past 7 years. Anyone have any solid advice on what he should do about this? Should he try to file all 20 years? Im in way over my head here.3. I have read about currently not collectible status. If someone has fd up this bad, is this even an option?4. Hes basically living out of his van at this point, with enough cash to cover his groceries and gas for the next three months. After he recovers from his surgery, would I be some sort of accessory under the law if I let him try to land a work from home job using my home internet connection until he makes enough to afford housing?Any serious advice would be greatly appreciated. He knows he has royally screwed up, but I believe he will do everything in his power to fix this. Is the tax part even fixable?edit: line breaks and added: theres no cash available for hiring a pro at this point in time.  <response>: Way to be a good friend. 