As others have stated, the team on the ground is the most valuable asset that you have.

Spending an hour with a CPA who understands your overall financial situations would be time well spent, but there are some general rules of thumb:If you hold the asset for less than one year, your profits are considered short term capital gains - which are taxed as ordinary income at your standard tax bracket rate. 

It tracks income and expenses, but not assets, so it wouldn't completely eliminate my use of QuickBooks.To populate Rentec I was looking to add a remote user (a VA) to my QuickBooks.

Medicaid isn't meant for people with assets to help them when the bills become big. 

What are the bare minimum requirements I should request in a written agreement/legal document with this individual to best protect my asset in case his investment fails or falls short.

Assuming I am correct (which I believe I am but consult your tax expert), there is no need for 1031 exchange.This would mean the money obtained via the sell would incur no taxes and can be invested however your Mom desires. 

You would still be able to depreciate the asset and use bonus depreciation on any renovations during the first year.

If at the end of the day you cannot obtain a solid answer to your question, I would not move forward until you know for sure what can happen, or at a minimum request an extension to the due diligence period to research further. 

When he went to get his building permits, they brought out an aerial photo and asked what the clearing and structure on the property was, and why permits had not been obtained?

He walks away clean with 10k or so in his back pocket and you get the asset with enough dough to fix the place and everyone wins .