I suspect this would happen if various parties were given the ability to ask questions in nearly every application for what this thread touches on - and I have major concerns about integrity (and credibility) issues involved in putting yourself in a position to defend this position if ever challenged. 

Law enforcement is now targeting third parties involved in “cooking the books” that “force by fraud” qualify clients for Covid-19 relief.

My biggest piece of advice is to connect with local chicago real estate investors in person...highly suggest checking out the christmas party on 12/12:  https://www.biggerpockets.com/forums/521/topics/1218823-chic...

You mention a traditional STR PM agreement where the upside is shared by both parties.

Many banks have been sitting on 2nd liens for awhile now due to compliance, regulations, and other third party risks.

Defaults and Remedies A default exists under this note if (1) Borrower defaults in the payment of this note or in the performance of any obligation in any instrument securing or collateral to this note; (2) (a) Borrower or (b) any other person liable on any part of this note (an "Other Obligated Party") fails to timely pay or perform any obligation or covenant in any written agreement between Lender and Borrower or any Other Obligated Party other than as described in (1) above; (3) any representation in this note or in any other written agreement between Lender and Borrower or any Other Obligated Party is materially false when made; (4) a receiver is appointed for Borrower or an Other Obligated Party or any property on which a lien or security interest is created as security (the "Collateral Security") for any part of this note; (5) any Collateral Security is assigned for the benefit of creditors; (6) a bankruptcy or insolvency proceeding is commenced by Borrower, a partnership of which Borrower is a general partner, or an Other Obligated Party; (7) (a) a bankruptcy or insolvency proceeding is commenced against Borrower, a partnership of which Borrower is a general partner, or an Other Obligated Party and (b) the proceeding continues without dismissal for sixty days, the party against whom the proceeding is commenced admits the material allegations of the petition against it, or an order for relief is entered; (8) Borrower, a partnership of which Borrower is a general partner, or an Other Obligated Party is terminated, begins to wind up its affairs, or is authorized to terminate or wind up its affairs by its governing body or persons, or any event occurs or condition exists that permits the termination or winding up of the affairs of Borrower, a partnership of which Borrower is a general partner, or an Other Obligated Party; or (9) any Collateral Security is impaired by loss, theft, damage, levy and execution, issuance of an official writ or order of seizure, or destruction, unless it is promptly replaced with collateral security of like kind and quality or restored to its former condition.

These studies typically if done by 3rd party would cost $10-$20k but you could also do it on your own.

Because the entity you could go after, who has little capital to go after, sure you could put them out of business, and wouldn't ya know it 24hrs later that property is now under a new same/similar enhanced NNN lease arrangement to a new separate operational party who took over for the now bankrupt entity.And what attorney is going to burn through thousands of hours, trying to go after "dry wells"? 

Tech for most part is just a deployment item not innovation, utilizing tech to automate and do, more efficiently, what was done in antiquated manners. 

As for gray areas in contracts, the courts will almost always find in favor of the party who did NOT write the lease.