He
owns a three-bedroom ranch-style house in Charlottesville, Virginia,
where he lives with his wife
and 3-year-old son, Benjamin.
He recently
made the last payment on his silver, Toyota Tacoma.
He likes his job.
Not bad for 36 yr old, at least he's still not in his mothers basement BUT
Can't figure out how to get out of debt ?

Bet you could have paid off that student debt a long time ago IF
You did not buy a house.(if your in debt 350G, you can't afford one)
Not have a child before being able to afford one (if your in debt 350G, you can't afford one)
Bought a new truck on credit (if your in debt 350G, you can't afford one).
Classic buy now, Pay later (aka spend more than you can afford)
With out the additional debt you accrued from the above, you most likely would not have to have "struggled to keep up."
Likes his job ?
No mention if that college education got you that job but I'm pretty sure the bachelor's and master's degrees you both received were not in financial planning or economics.

Hi, Mom ?
We're moving back into your basement.