Yeah, kind of figured when you said he was under water. He bought right before the bubble burst. I was so happy when I sold my only remaining rental around that time. My nephew wanted to buy a relative's home and did despite my warnings. Fortunately, they wee offered the house at 35% below the current market value so the hit wasn't as bad as it could have been, but a hit non the less.
I had found a 100 year graph of house prices and knew there were problems. I even showed them the graph but what did I know. Anyway, I told the people managing it that I was thinking of selling and they quickly offered to buy at what I considered a great price considering I was avoiding selling fees. A year later, I ran into the agent and all he could talk about was the hit they took on that purchase. I told him not to worry, the prices would come back, but I had a smile on my face after we parted. I suppose by now it's worth what they paid or at least close, but they won't sell it anyway so no big deal.
I just feel bad for people like your dad who not only got hit by the bubble but never recovered. Apparently, it's happening again in some area.