When you mention “tax strategies and considerations,” are you referring to buying a primary residence or an investment property?

Liability Considerations:● What are the potential liability risks associated with operating a short-term rental andsupporting a non-profit on the same property?

Even if it is across several cards4) What are some considerations to think about before doing this?

Of course, investment considerations should always take precedence over tax considerations. - ie don’t buy a dog property to save taxes.While BP is excellent in many ways, I would caution you against accepting free advice from people you don’t know on BP when hundreds of thousands of dollars are involved.In my mind, better to spend $10,000 to get advice from someone who really knows this stuff.

The money up front is called the "option consideration". 

Other considerations: Who is guaranteeing the loan?

Hard money/private loans are considerably less work and labor-intensive than an FHA or VA loan, as well as close much more quickly, so I can see there being a differential in comp between those. 

All options are considerable, townhouses, condos, or single family.  

And took into consideration the potential for increase with minor improvements.

I seem to remember that when you do a non-arms-length transaction for token consideration (I'm certain you would have to have some sort of consideration in the sale...like $10 or $100...ask your CPA/real estate attorney/title company).that you might have to pay the Florida Doc Stamps on 1/2 of the mortgage balance.