Whats the best way to sell a property like this to minimize taxes, his CPA has told him about Charitable investment trusts, his mortgage guy told him about reverse mortgage, and his financial advisor is trying to sell him on a Private REIT that he can 1031 exchange into so he's confused.

What I learned is there is intense competition for charitable giving. 

For Schedule A you have $10k of taxes (your residence plus SC state taxes, capped at $10k combined) plus whatever mortgage interest on your residence (if any) plus charitable donations.

@Will Barnard I'm new at CRE but id look I to putting the place into a CRT( charitable remainder trust) this way you can defer tax payments.

This is why I have no problem with my socialist friends being in charge of charities so long as they don't get in my way when it comes to making money to fund their charitable work.

You will need to get an appraisal of the property after you subdivide it and before you donate it to support your charitible deduction. 

Property held for investment would be taxed as capital gains (unless you defer the taxes through a 1031 Exchange, 1033 Exchange, Charitable Trust, etc.) 

Usually, there are companies that pull money together from investor like you in a partnership and you would get the K-1s from the partnership with huge charitable deduction. 

Commercial gatherings, including but not limited to luncheons, banquets, parties, weddings, charitable fund-raising, commercial or advertising activities, or other gatherings for direct or indirect compensation are prohibited; g.

If I feel charitable, I think I would rather donate to a good cause than rent to a person that has that type of credit score and detainer.