Erica, that was my sentiment as well. 

People in the area can't qualify for a loan, the neighborhood itself isn't desirable and he has sentimental value tied to the houses. 

I want outside perspective since I do have a sentimental value on it with many years of sweat into the place.

My sentiments exactly!

Guaging local sentiment will be key.

I echo @Steve Vaughan sentiment on the multi.

Hi Sam,Just to echo Ed's sentiment, it's all about the contract.Good luck! 

I agree with the general sentiment of this post, but I think he's a bit black and white in analysis.  

It'd be great to rent the place out down the line but I'm not even concerned with that, unless of course it really just doesn't work out with me being happy living there.The general sentiment that I've been hearing is that now is a great time to buy still (low interest, qualify for loans, etc.) and that time is "running out" so to speak on Downtown properties because value is continuing to rise.

In my shallow research so far I've seen a lot of people mention similar sentiments in terms of Canada not being the best for it.