If you are comfortable breaking even for a bit while betting on appreciation, it feels like a decent gamble.  

Harry Gamble I appreciate the advice and will look into what a title company can or cannot do for me in this situation!

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. 

What if you had an ulterior motive, i.e. winning by losing (building credibility through perceived authenticity and vulnerability)?

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.