I don't see a problem with gambling your own money, but taking huge risks with other peoples money is irresponsible and reckless.

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.

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, ...

The Kansas City Chiefs' triumphant victory in the Super Bowl not only ignited celebrations across the city but also sparked discussions about its potential impact on various aspects of life in Kansas City.

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