You say Most people are probably looking to spend a couple days here versus a whole week...That likely means people would be more inclined to book weekends over weekdays which will leave the the bulk of the month unrented.

Further, they moved in on September 7, 2018, and the first inclination of a bug issue occurred via text a few weeks ago.As far as inspections, I don't have specific dates, but I do give them 24-hour notices that I will be stopping by.

However, I would be inclined to tell any tenant that all or a percentage of the rent can be applied toward materials used to improve the property, - if the tenant will provide the labor necessary for improvements.   

Although I am inclined to believe that you are not able to manage property in the scenario you detail, I honestly do not know.Nathan is correct in that these questions are appropriate for an estate planning attorney as they are complex and potentially involve assets of significant value.

Now it is worth 10x what he bought it for (based on my cost estimation software I use in my industry and knowing the cost per sq ft very well in my area, I am inclined to believe he is very accurate), he states he just wants X dollar amount for it and even after the gifting of the down payment, there is easily enough equity remaining to make that happen.I don't ever want to acquire or amass wealth through shady deals or taking advantage of anyone, so I know the statement of two players playing each other is a false one.

If they know there is a high likelihood they will get a project, they will be more inclined to give you the estimate for free. 

My first inclination is to refinance as soon as the project is done.

Background is in dealership management, nationally recognized, so I'm great at closing/negotiating, numbers, and navigating a deal, and I'm naturally more transactional inclined. 

If it's double, I might be inclined to do black or white instead.

Also, I’m becoming more inclined to consider higher rents but still in B Class neighborhoods.