How would one go about establishing the value of an abnormal property? 

This pursuit has been incredibly fulfilling, engaging and eye-opening; significant relationships have been established and I've even acquired properties for myself along the way. 

I plan on getting into the flip game much once I establish a few rentals that cash flow.

I was of course intrigued by this process and soon realized that this was called wholesaling.  10 years later I have established my own business doing this.  

Ridgley's Delight is a well establish area with value that is likely to keep it's value or appreciate.

Establishing a personal relationship with them is most important.

Once you have your goals established, then creating investing criteria to support those goals is much easier and drives confidence.

Take a gamble on birdtown for cheaper property? 

I think @Jay Hinrichs touches on the important point... if you can reasonably expect appreciation, then it might be a good bet/gamble. 

From day 1 I established a mgt co s-corp to manage my own portfolio.I use it very little the way you are outlining, though.I do not want to take beautiful SE-free passive income and turn it into active income.