It is a sad story. I'll agree to that. That being said,
1) the guy has an awesome pension waiting for him when he reaches normal retirement age. Like, AWESOME!!!
2) The guy made some not very good decisions that were very avoidable. First off, he had 8 kids. While this doesn't immediately bring down the facepunch hammer, it does make it much much harder to limit your expenditures especially when you decide that you're going to foot the bill for college for all of them. He also decided to take 2 years off to be a parent (good on him!) but didn't do the math on how much his lifestyle cost and how long his savings would last. He could have found a job that paid some money but still let him be a Dad. Heck his wife wasn't working at that time either.
So he had 8 kids, and the house and expenses that go with that, and lived in a super expensive area because the schools were better, then decided that BOTH parents shouldn't be working for 2 years!!! Heck he even said they had 500k saved at that point. To go from that to homeless means that they continued to spend $250k per year even when BOTH parents weren't working. There were some bad decisions at play here.
Good job though on figuring out how to cut expenses and earn money through craigslist gigs. Glad things are getting better for him. I hope he learned something about big finances.
