I disagree or simply don't understand what you are writing here. The demographics do not preclude everything but a dive bar. Within a 10 minute walk there is surely more than 1000 people earning more than $75,000 gross income per year. Add on a 10 minute streetcar ride and you get even more. What is on offer and at what price will determine what the atmosphere of a bar in this location is like. The Drake was purchased by an investor in 2001, at a time when the "West Queen West" environment was similar to what Dundas East is now. I personally predict the future of this neighbourhood to be on the same track.
Jonny5, maybe I wasn't clear. I'm not trying to dictate anything, merely pontificate on positive possibilities for this property. What is the best outcome? And what is the most likley outcome?
There is no track record of a non-dive bar succeeding at Dundas & Ontario. People who open bars usually want to succeed. For anyone looking to open a bar in downtown east, location is a top priority, and Parliament St. in Cabbagetown proper is the preferred location. Nice bars (that is, non-dive bars) tend to be clustered on vibrant commercial strips. It would be great if something House on Parliament-y opened up at Dundas and Ontario, but I think most prospective customers would rather go to the main shopping area on Parliament.
On the other hand, some landmark bars can do well in odd areas (the Dominion on Queen at Queen & Sumach comes to mind). Alternatively, it would be great for a trailblazer-type business to open up, in the vein of Upside Dive and Ecostems at Queen & Sherbourne.
To your second point, I don't see how rooming houses are more profitable than "800 to 1000 sqft lofty apts.." Given the Toronto market, I would expect renovated and well designed units to fetch a massive rental profit in comparison to what a (legal) rooming house could get.
Rooming houses can be really profitable which is why there are so many. Let's look at an example:
http://www.realtor.ca/propertyDetails.aspx?propertyId=11184551&PidKey=-1585487757 . Figure $500/mo for each of the 8 units ($4000/mo income) on a $2000/mo mortgage. Figure $400/mo for utilities and another $300/mo for property tax. And zero capital investment because no matter how nasty the units are, they'll be rented out somehow. I don't like rooming houses any more than you do, but as long as they're profitable they'll be around. Here's another example:
http://www.realtor.ca/propertyDetails.aspx?propertyId=11149132&PidKey=1969581919
Renovating the existing building into condo-type units and selling the units off could be risky, and tricky. My suggestion was to create a rental building with several nice, large units aimed at yuppies. This would be good for the neighbourhood, but unlikley to be as profitable, or as easy, as a rooming house. Turning this building into 4-5 nice apartments would require at least a few hundred thousand in capital investment.
In the end, we have to assume our friendly investor cares about profit and nothing else. What do you suggest he does with this building? And assuming he's driven just by ROI, what do you think he will actually do?