I just remember when that list of wrestler's salaries was floating around a while back that Matt Hardy was making about $300K a year. Now Jeff's a little higher on the card now then Matt was then, but he also the lacks the seniority that some of those other top guys have that make a million. I wouldn't be shocked either way.
Also, if Jeff truly lived in a trailer, then it's not that surprising that he wouldn't have insurance. Yes, it's always a good idea to have protection, but on a place where there is minimal or negative equity build over time, it wouldn't be that unusual to not have it insured.