Bob and Barb had a lot of problems as a couple. Either they got hitched because of the pregnancy or Barb set out to have a baby because she was fearing Bob would leave her. It's unclear where Barb lived before she got with Bob, but I think she was living with a family member or in a small space where her hoarding wasn't really extreme yet. I can totally imagine Barb walking into 14BC back in the early 80's and seeing a beautiful palace that was all hers. I'm assuming Bob owned and lived there alone, having possibly raised his adult children there years prior. It's big enough for a whole family, yet Bob creatively designated specific purposes for the extra rooms. I don't think it took long for Barb to start filling rooms up with Barbage, and of course Bob went along at first thinking he was allowing her to settle in and make the space hers and his as well. I think it took a few years for Bob's optimism and hope to completely dissipate. He probably woke up one morning to see a teenage Chris dancing in front of the TV like a girl while watching Sailor Moon among piles of Goodwill junk on all sides of him, and Barb belching from the orange chair that she appears melted into, using her Atkins diet book as a plate for a McDonald's burger. It was at this time that Bob imagined the bachelor pad he once occupied at 14BC, the clean house with a large music collection neatly stored in its own special room, and how he traded it for a woman who would take it all from him in exchange for a couple of screws in the early 80's and a retarded gay son. Bob was a simple man from the South, and I don't think he was a particularly hateful person, but he didn't want his son to turn out gay. He already had to deal with a pretty serious disability, and in his dying days Chris' choice to go Tomgirl only said one thing to Bob, and that was that all of Bob's suspicions were correct (even if they weren't, Bob wasn't about to just "accept" his straight son's feminine tendencies). To Bob, he raised a flamer who can't support himself, he enabled a hoarder he grew out of love with, he trashed his house by being ineffectual to his wife, and he died in pain and discomfort in a garbage pile. Seriously, if Bob became a ghost, he's haunting the remaining Chandlers out of revenge.