I've actually seen this cow in the wild, albeit a few years ago. I actually knew of him, but I had no idea he was a major lolcow- he was a very prolific blogger, and would tag his blog with absolutely everything remotely related, and I stumbled on it completely by accident. It is not interesting in the least, unless you are fascinated by apartment building garages.
I was on the streetcar, and he was standing in front of it, awkwardly trying to film it. He hustled to get on, and was walking with a medical cane which he obviously didn't need and was set too short to be of any use even if he did. He fumbled and took a long time to pay with all change. He looked like he hadn't washed in several days and his coat looked like it hadn't ever been washed. He tried to strike up a conversation with the streetcar driver, who wasn't having any of it.
He sat in front of me, and he smelled like a mixture of sour milk, wet dog and BO. I had a transit pass, and I really didn't want him to talk to me , so I got off and grabbed the next streetcar.
As for his bum-like state and teeth, I can at least partly explain. Toronto is a very expensive city to live in, and the apartments Rootbrian lives in are some of the worst in the city. They are inhabited almost entirely by people that don't have any choice- ex-cons and gang members, immigrants who don't know any better or were tricked into it, and welfare recipients who are waiting for or don't qualify for social housing. The rents are cheap, the landlords don't do credit checks, and they'll take anyone with a pulse, first and last. 3 people on welfare and disability would be able to afford it, but anyone who was able to would move.
The teeth are a bit harder to explain. In Ontario, dentistry is covered by government healthcare up to your 18th birthday. Thereafter, it isn't. Most employers - even a lot of part time ones cover dentistry, and a child can stay on their parents' plan to age 25. Self- employed people like real estate agents and lawyers can get group plans or private insurance. Welfare will also get you access to low cost dentistry, and many dentists work on a sliding scale- so, there's no chance that he wouldn't have found a way to get dental care except by consciously avoiding it.