It will be easier to get on a call and discuss because this can be a long conversation

Exactly it - it is that process of moving the property from a corporation to a pass through entity that will trigger that gain, and it is NOT the conversion of that entity for state law purposes to an LLC that triggers the gain.While you might think of this wholly owned S-Corp as "just you", for tax purposes it is entirely separate from you.   

I personally wouldn't go as far as to call them shady, but there's definitely been some fees and hurdles that weren't exactly laid out during the initial conversations and I'm in no way questioning your use of the description. 

To me, this would have never been the conversation a few years ago when rates were more comfortable for the average investor (likely 5% and below), but it is the reality we are in now!

Never engaged in conversation.

I didn't fully understand the conversation though, so let me ask specific question. 

I spoke with Laura Montz from Cogo at length (over 1 hour) and asked at the end of our conversation how much?

This is certainly text book and absolutely the proper way to analyze a deal.Im not sure what he owes on the home but based on the payment and the year it was bought and the fact that its 20 min from Austin im just going to throw out 500K for conversations sake.500K compounding annually at 3% for 5 years comes out to approx $578,000, and you have the loan paydown aspect as well obviously. 

If you tell him to quit you can find someone else but it would certainly be more as contractors dont like to start mid project like that and finish someone elses' work but its best that you have a more constructive conversation with him about his absence.

There is also a facebook group called alabamahoacoa that has conversations about these universal issues.