Why does KW region stand out compared to the rest of Canada (especially other metropolitans outside of GTA and GVA )? 

I'm not sure what banks look at when acquiring for a new loan but would there be anything that would stand out on any tax form that may require for a future loan?

The home value spike of 2013 to 2016 can be significantly attributed to cheap money.

The best way to value 3-4 unit buildings is using the sales comparison approach with nearby sales comps with similar attributes to the property.

A major negative is that when you strip away the industrial era attributes like water transportation, hydro electric power, relative cool summers ( an industrial neccessity before air conditioning), a semi skilled work force, and the advantages of having a geographically concentrated industry, you are left with a city with a high level of poverty, a low level of education, a corrupt and ineffective government and very bad weather.  

I'm doing something similar where I'm planning on putting very nice finishes in a smaller house to make it stand out from the others and I am curious how it worked out for you.

That would make your offer stand out from any others.Good Luck!

And when you get into the negative in REI it seems to be a lot of negative when it happens.Even though I have my market data, DOM's, and know the theory of how to make a house stand out from the competition in terms of style and what not I just have a fear that it will take much longer then 4-6 months to sell.Is this irrational considering DOM's in the neighborhoods I'm targeting are around 81 DOM?

There is nothing different about your letter so why would it stand out? 

That just goes to show you that this area doesn't need much in the way of updating to make it stand out amongst the rest.