None of my business, but from your description of him, I wouldn't waste my time and money. I've known a few guys like that, they usually get it eventually. I learned to both drive and ride before age 10, got both my drivers license and motorcycle endorsement on my 16th birthday, worked on the farm from age 5, bought my first dirt bike with my own money at age 8, and have been continuously employed since age 18. I did mess up a little bit in high school, hung out with the wrong "friends", and let my grades drop. I still got my diploma, just a couple months late, and had a job 2 days later. I had no choice. I had rent and car payments to make, clothes and food to buy, and would have been on the street real quick without getting a job. I lost the part time job I had when I bought the car when the guys running the place, an auto body shop, all got arrested for selling stolen car parts. My dad made the payments on it till I could get my diploma, and I paid him back, every penny.
I won't spend more on a bike than I think it's worth, but if it's a good deal, I don't seem to have a problem buying bikes I don't need.
2002 Vulcan 750, 2013 Royal Enfield B5
2001 XT225, 2009 Genuine Stella
1980 Puch moped