I am doing CFO/CIO work with some GCs in different states and trying to figure out what kind of software might be useful for enhancing the business, but the work is mostly restoration. 

Try a simple exercise with him of listing all the financial considerations and purchase/management activities that you can anticipate today - who will do what, who contributes what - consider putting all this in writing in some sort of operating agreement. 

My target property for an Agritourism project has a ~$1.3M forestry grant for understory maintenance, ecosystem enhancement, and wildfire mitigation.

That should come from the why.If you have not already done so read Anthony Robbins awaken the giant within and do the written exercises in the book . 

This congruency not only enhances the transaction but also reflects positively on the RE agent, making them look good in the eyes of their clients.Moreover, going above and beyond means exceeding expectations.

My biggest concern was the "Due on Sale Clause" but I have had an off the record discussion with my mortgage banker and he put my worries to ease (along with all the other threads that say the clause is never exercised).

(or errors by the title examiner/title company).You wouldn't have title insurance coverage for mechanics liens under either scenario unless you purchase an enhanced owners policy (or paid an extra-hazardous risk premium).

I love the enhanced Airbnb income, but, there’s regulation / ordinances in the City of Chicago that add risk to scaling an Airbnb portfolio there. 

However, when you dig deeper, or speak with local turnkey providers or real estate agents in Memphis or other cities, it becomes more of an exercise in seeking out which areas to AVOID and which areas are really able to provide a safe haven for your investments, and more importantly, peace of mind. 

Example external storage area conveniently located where it can be converted to a walk in closet as a later time.Part of the exercise is knowing the various regulations.