To me it seems like a gamble.

Church Hill is one of the top up and coming neighborhoods but the deals are in the rough sections, which may get gentrified but it's a long wait and sort of a gamble in my opinion.I'm looking for a SFR now to live in and rehab, preferably in any decent area.

Do not disregard looking in the city of Milwaukee as well - there is a number of pocket neighborhoods, typically where it is on the border with a suburb, that should give you a good rental and hold the value for a while.Duplexes typically do not cost more than SFR, but will give you double the income.Enjoy sunny Cali, as it it raining cats and dogs around here!

I don't know how the cross-border details would work, plus with the CAD low right now, it might not be good.  

Laws and practices change from one town to the next, across state lines, and across international borders.  

I like the concept of real estate being able to control a tangible asset that can have multiple sources of profit where as stocks is slightly above gambling. 

(BP does tend to shake its collective head at such a "gambling" approach).Me?

So, if you are comfortable with month-to-month and gamble on what happens after closing, then do nothing.

After flipping several houses this year in my home territory of Ontario I am now starting to look south of the border for flip opportunities.

We are right at the border of 1431.