You're exactly right. No company wants a new 44-year-old employee because no company wants to pay that employee's health care bills, and at age 44, looking for a screams "loser". That doesn't mean there isn't a ton of work out there for 44-year-olds, however, you just have to find a way to get it without resorting to the "income with training wheels" mechanism of a job.
At 44, this guy should create his own consulting company like I did and find a few un-employed IT guys and send them out on contracting gigs. With 20+ years of experience, why is this guy NOT in management? Companies that hire H1B consultants can write off their pay as business expenses. Employee salaries and bennies are treated differently on the books.