I bought the house last week for 20k including delivery so I figured it's a gamble I can live with.

It shows authenticity and proves I don’t need to impress them with image.

Don’t be afraid to gamble with nothing just be smart about your bets and smart with your winnings.

Saying your tenant is paying the interest on your mortgage is like saying you can gamble at the casino when you’re ahead because you’re playing with the houses money.

In a rapidly rising market, some investors will pay more in anticipation of appreciation, but I call that "gambling".  

I called several of his references, and they had nothing but positive comments on the guy.We decided to take the gamble and negotiate a contract with the guy.

The only possible cash flow strategy I can think of is to gamble on rent control cities by buying out tenants to make the numbers work (much harder in SF now).

The only way for you to truly make money on this property is through appreciation, which is essentially gambling, but a lot more work. 

It's a gamble I suppose however these types of tenants can be big problems.

I believe there are plenty of careers that provide high levels of personal satisfaction and are not part of the so-called rat race.If you find yourself in 'job hell' there are several avenues out, none of which involve gambling your time and money on building a business which statistics say will probably fail.Living below your means is a tried and true method of building wealth.