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Where is "Daddy Divorceville"? What's the most awkward floor plan ever? Can a new Starbucks location save an old neighbourhood? What street has the most speed bumps? And what might be the most "unsellable" street in Toronto?

Since 2007, Bosley Real Estate sales representative David Fleming has been providing the laugh-out-loud answers at www.torontorealtyblog.com, along with personal anecdotes, analysis and opinion-pieces.

"I didn't know what a 'blog' was," he says as we stroll the St. Lawrence Market neighbourhood, which, coincidentally, is where we both live. "I thought, 'that is the dumbest word I've ever heard' and my buddy kept saying to me 'You've got to start a blog!'"

Approximately a thousand entries later, Mr. Fleming says – with only minor exaggeration – that he "might not be in the business today" had he not listened to that friend. "I do 60 deals a year, and maybe two or three aren't somehow traced back to the blog."

So, what's so special about it? Well, in addition to some very funny entries, Mr. Fleming doesn't pull his punches when editorializing, despite raising the ire of certain condo owners. For example, he caused a stir when he wrote that the 20-odd buildings of CityPlace will become a "ghetto" in a few decades due to their isolation, lack of amenities, and large percentage of investor-owned units; condominiums that charge high maintenance fees but have few amenities have been called onto the carpet; colleagues accused him of being a "whistle-blower" when he criticized artificial bidding wars and other questionable moneymaking tactics that, while perfectly legal, leave a bad taste in buyers' mouths; after comparing a newly converted, century-old foundry building on Lansdowne Ave. to Alcatraz (because of the contrast between its soaring atrium and the tiny front doors that lead to tiny units) he watched as his inbox clogged with angry e-mails.

"Most people don't have opinions in my business," says the 31-year-old matter-of-factly. "Someone wants to see [a bad place] you know what most people say? 'Great, what time do you want to go?' I don't do that, I write them back and say 'Here are eight reasons why I don't like it; here's four other buildings that are better.' That's my value, that's what I do, so what the hell is everybody else doing?"

Some of his opinions are more useful than controversial. As we stand and admire the variety of shops and services clustered around his "favourite block" of King St. near Sherbourne, he tells me about his "A-B-C" theory: "King street is an 'A', it's got all the high-end furniture shops, all the coffee shops, all the restaurants, it's on a TTC line, it's where you want to be and it gets an A," he says. "Adelaide is a block up, so it gets a 'B' [since]there's no real infrastructure and you're walking to King."

Walking north to Richmond, he assigns it a 'C' because the condo inventory is older and it's further still from the shops; he also points to the "invisible fence" to the north that separates affluent condo-owners from the "dodgy" Moss Park dwellers along Queen St. East, which is "a completely different world…it's one of the biggest juxtapositions." As if to back him up in bricks and mortar, the sold out "The Modern" condominium, with its distinctive blue-black brick, sits cheek-by-jowl with a dilapidated two-storey building.

We agree, however, that The Modern might resuscitate the failed project at the corner of Sherbourne and Queen (formerly called "Kormann House") as the invisible fence may have been pushed just a little. This is good, as the heritage building on the corner would have been sandblasted and incorporated into the new condo's base (and, as a very biased aside, I hope the fence has indeed been pushed, as my wife's vintage furniture shop, Ethel-20th Century Living, has just relocated from Leslieville to Queen near Parliament).

And speaking of heritage buildings, Mr. Fleming knows his stuff. He frequently interrupts our conversation to offer enthusiastic tidbits about which buildings were warehouses, stables, tanneries and movie houses; he even points to the exact location of the start of the Great Fire of 1849.

On the lighter side, he eschews the popular notion that a No Frills or Dollarama signifies a low-income neighbourhood as he trumpets new locations for each at Front and Princess streets: "I get my 200 bucks of stuff for eight bucks," he laughs. He reveals that Daddy Divorceville is a new subdivision where old factories once stood near Eglinton and Laird (look for the video on his blog), that there are more unfurnishable triangular floor plans in Toronto than one might think, that he's counted all fourteen speed bumps on Merton St., and, finally, that he thinks poor Percy St. in Corktown may be the most unsellable.

Later, as we walk along Front between Jarvis and Yonge, we stop to daydream: "I'd love to own an old building one day, to be a part of it," he says, looking up at the 1872 Beardmore Building. "Look at the brick, it's so well kept…they don't make it like this any more."

And judging from our very pleasant architour, I'd say they aren't making many real estate agents like David Fleming any more, either.

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