I know that you do a great job smoothing out any "rough spots" in the lending process, so that certainly helps when the deal starts to go sideways... 

Negative CF, which is what you are describing, means you are buying your property, and making no money in the process.

Right now, I am an aspiring real estate agent specializing in investment properties while also in the process of developing an app!

If, through the process of renovating the property, the market shifts, do you have an alternate plan for the property, whether it be to live in it until the market improves, or convert it to a rental property, etc. 

I realize I am not cut out for the entire REI process of consistently finding multiple properties for particular exit strategies. 

First time in 3 years we have had to file a claim with over 150 airbnb stays. Guest left all windows and door open in our cabin in -15 degree weather when they left causing a frozen pipe. Left the place destroyed and ...

I would just add that probate isn't really a painful process in most situations.

I like the notion of protecting peoples privacy to process.

I say take a gamble for anyone in which its even possibly feasible for and trust they're process. 

A variety of things could have caused this.That said, what you've described above is not so untypical in terms of the steps of the process for a fix and flip loan.