I can "cash flow" more from my stocks/index funds and high yield savings account with far less stress. 

Welcome to Bigger Pockets @Joshua KeimAs a fellow Memphis native, I’d love the opportunity to connect in person and discuss strategies with you!

It separates your personal assets from your business, providing a safeguard if any legal issues arise related to tenants or the property.

Not that it cant or wont, but unlikely.If OP applies for homestead on a new property, then I personally would not lie during the application about receiving the exemption on the existing property.

Even when I did reach them the first time,  the other person on the other line sounds like a moron who doesn't know how to help. 

By any chance, do you know if you're eligible for any government grants and/or funding?

@Sonya Sharova I haven't personally done Frank Rolfes boot camp but I have heard it's great.

The big opportunity here is creating a scenario where both parties come out ahead, especially in situations where the seller might otherwise walk away with little or no proceeds.If you’re considering moving forward with this kind of structure, I’d be happy to assist with running the numbers or exploring funding options to make it happen.

Personally, I think this company is probaby about to go out of business - they have lots of inventory, and it's not exactly prudent to be investing in FL in the coastal areas now anyway.  

- If the Association Fees are regularly increasing or the Association is poorly funded - SELL.3) How much of your TIME do you want to invest in all this?