We're fortunate enough to have capital and credit capacity.We have experience investing in student properties and thus started our search around the Johns Hopkins campus (mainly Charles Village, Old Goucher, Remington and Barclay) to see whether we could find promising opportunities.

The areas we are looking in are: Humboldt Park, Avondale, Ukrainian Village, and Pilsen.  

Auto correct.  

So the box Vinyl Village type homes is the current build (mixed in with townhomes, duplexes, quads).

Because this age automatically (or auto-magically) gives you credibility with sellers, contractors, lenders, and real estate agents.

I was hoping a couple Chicago Investors share would please share their experiences with investing in Sauk Village, Chicago Heights, and Dolton?  

There are morepotential options if you are bringing your primary home and auto insurance along as well.  

In Toronto proper I keep thinking Weston Village is an area to watch for gentrification, but my wife won't agree to buying there because she thinks the areas around it are too rough!

Additionally the mortgages, if you have them, can be put on auto pay through the bank account.Hope that helps.

Detroit is partly the victim of economic trends far beyond its control, the downsizing and outsourcing of the auto industry and the collapse of the sub-prime bubble, to name just two.