That is why I responded to this thread and have given a concise reason to support this position.I am not a wholesaler and I have never purchased real estate in the US and I don't profess to know the intricacies and differences of laws south of the border.

I will spend thousands of dollars on travel and dining and las vegas gambling, but still wearing the same clothes I have been wearing for ten years because I am too cheap to pay for clothes.

The best way to determine this is to consult with a good cross border tax & legal specialist who also know the intricacies of holding real estate in the US.  

You mention the "Contractor Wildcard" as a gamble.  

Cash flow properties are safer but I don't think investing in equity growth is "gambling" as many people state in REI forums. 

My wife and I have a small buy and hold portfolio in Memphis, and we would much rather hold on to a good tenant than raise rent and gamble on a tenant leaving, i.e. avoid the tenant search, lost rent and turnover costs associated with a changeover in tenants.

Playing the appreciation game is a huge gamble, with a lot of unforeseen future moves with rates and segmented markets. 

First things first, let's talk city borders and real neighborhood borders.Despite what the Pittsburgh neighborhood map says - Brighton Heights as a neighborhood ends when you go across the Shadeland Avenue Bridge or down into "Woods Run", which is not technically a neighborhood, more defined by the valley between Brighton Heights and Marshall-Shadeland -the values and housing stock down there are VERY different from those up the hill.

When you invest for appreciation, it is more like gambling, because there are so many factors.  

https://www.wlky.com/article/online-sports-betting-kentucky-...
This should help bring more tax revenue into Kentucky and less money going out driving across to Indiana to place bets. Hate the brain drain of it all, ...