Insurance premium of $1,200/yr seems a bit high, at least compared to what I'm paying in Maryland. 

But each person needs to figure out their own level of risk vs reward. 

The REO world has several differences compared to retail Real Estate.It is common for the listing agreement of an REO property to have unique or interesting provisions that allow an assigned agent to continue marketing a property as active (even when the seller accepts an offer) until that buyer has performed and the property is sold. 

Honestly, I am looking at cash flow and appreciation as well, I think the RE prices there are very low compared to anywhere else in Southern Ontario and there is a fair amount of room for appreciation.

How do you more seasoned investors go about getting comparable sales data for a potential off market deal? 

They are a great resource at a reasonable price comparatively.

I must concur architecture is a tough profession that requires a lot of you, but can be rewarding if you have the passion for it.

None of which are required for school work.You can offer a differential if she wants to pay for premium internet, otherwise tell her “No” and stop getting aggravated or rewarding her complaints

Although the average of these 2 areas is around $950, you will clearly be getting very different rents in each of them.The more specific an area (and similar the properties) you can look at to compare rents, the better your estimate will be.

Upper Kensington comparing to "rest" Kensington and Philly generalI have difficulty finding a tenant to an Upper Kensington home that is well maintained (new wood floor etc) and furnished.