I will do more studying on the actual risks of damages like this. 

(I’m 6 chapters into the IRC book and am studying other codes cause I can’t take hackjobs)

I have always assumed that this means if I make say 40K at my W-2 job and have a lot of rentals which with depreciation (or say a Cost Segregation Study) show a loss of 50K I can take my taxable income down to $0 and then actually down to a -10K, but if those losses were 80K, I could only go down to -25K, and then the remaining 15K would have to be carried forward.

So before you answer that question, you should perform a demand study to determine the ability to sell the homes. 

I wanted to see if anyone has participated in a coaching or mentoring program where the coach goes into these metrics in-depth with a case study.

And when you also have to prove intent to hold it's a whole different can of worms.  

You can't necessarily prove that you know the entire process, and certainly can't know how to handle every situation (that what "professional" are for, right?). 

For me, the tax preparation alone proves this out.

IF the Owner's buyer signed an Earnest Money release form, which usually includes a statement that the Buyer agrees that the contract is null and void, this could/would be helpful in proving/evidencing there is no legal cloud on title UNLESS the previous owner recorded the contract/lis pendens and it was never released and still of record. 

I've been studying/learning real estate for the past 6 months and I'm eager to take action– primarily with wholesaling.