Not agreeing that he is unemployed, but those people exist. Welfare, perfectly possible, I have seen it done easily before, slowly but surely and there are some ways to crack the system.
Leveling is pretty easy if you have played for a long time, getting the level cap for your characters each time it increases. Like he could of had all his accounts at 190 already from the last level cap.
Couple other things could of been for even smart people or just other options...
- Laid Off
Recovering from a work related injury
Living with parents (I don't know his age, could be 16-17 for all I know)
Bumming on parents
Study smart and in university at a dorm with lots of free time
Homeless shelter and rather not be middleclass (Met a homeless guy that said homeless are treated better than middle class, always being in debt etc.)
How did he get what you said he would require?
1. Gift from a friend/family member
2. Free wi-fi from burger king or a cafe