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. 

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, ...

With each passing year, I become more conservative and love investing for stable cash flow rather than gambling on appreciation.

Hi allI am a dual UK / US citizen currently working in the UK.

You'd be gambling that you found every billable issue because you know that you'll never see that money again once it walks out of the door. 

This would be an owner-occupied dwelling and buyers are in the UK.