Pickering St. still exists. It's in exactly the area I thought he might have gone to, by your story. It's just a couple of miles from where I live, so it's an area I'm familiar with. I would guess that the houses there were built just after WW1, although some are older, especially the few that are former farmhouses. The area would, broadly speaking, be called "the beach" nowadays, not too far from Lake Ontario, Victoria Park and Gerrard area. At that time, it was settled primarily by British stock, probably working class, although I will have to take a look at that particular street as there are a few streets not far from there that are quite luxurious. There were a lot of fish and chips shops in the area! within my memory, the last two of them have closed. It's very likely the same house is still there. I will go take a look after Christmas.
I don't know anything much about directories and electoral roles here, as I have never had to use them. I am the first person in my family born in Toronto, so I've had no need to dig any deeper. However, the site for the Toronto Public Library is
www.tpl.toronto.on.ca Their reference library has excellent resources and a strong local history collection. They will answer inquiries by email. If you look into it and find out exactly what you want me to check (preferably with a call number), I will go and get what you need. It probably won't be until after the holiday, as I was just there today.
It's hard to know exactly why he came here, but, as I said above, there was quite a contingent who settled in that part of Toronto at that time. If he didn't own land, he would have had much better opportunities in the city than working on a farm or in a small village. My lot had been on their farm since about 1830, and they were typical. He would not have been able to afford to buy a farm at that point.
There used to be a small Hunt's Bakery chain in Toronto, long since absorbed into some conglomerate no doubt, but they were around when I was growing up.
I don't think we have ever had (until very recently) a standing electoral roll. There was an enumeration for every election.