Why? That would make him mentally ill, having substance abuse problems or grossly irresponsible. I do not see why any of the three is desirable in a president.
2) Has been to jail or has a felony conviction.
Why do we need to have an ex-con president exactly? What is gained by that?
3) Had kids and were unable to meet their needs.
Which would be a testament to personal irresponsibility. Why should we encourage that in a president?
4) Drove to work without insurance because of an unexpected expense.
Another grossly irresponsible think that we should not encourage in our elected leaders. Unless you are talking about their misspent youth, things like that should disqualify a potential candidate.
The still have payments on the car and without the car can't get to work.
What's wrong with having a paid-off car?
5) Broke a federal law by jumping on a freight train and taking it cross-country.
Why should we encourage that?
While a necessary public expenditure for many, I do not see anything positive in having to have used them.
7) At one point in their life they experimented with sex and drugs.
All three of the last three presidents have admitted to having had experimented with drugs in their youth. And sex is not even illegal in most cases.
8) One with a mental illness. A mentally ill president would be wonderful as long as there is a doctor that can transfer power to the VP at any second.
The rest of the list was just boilerplate bleeding heart, but now you are entering full on Poe territory.
There must be at least one of him in the US.
10) Had a shitty demeaning minimum wage job for at least a year.
Does high school and college count or did he or she have to support themselves (and all the kids from #3) with that job?
How about
11) Is not a college graduate. Bonus points if he has GED.