To that end, in most cases even if the properties are owned within an entity, the principles (investors) will need to personally guarantee the debt.

Look online to see if any properties are being offered for sale or rent with a legal basement unit and you may get a tip off.

Directly investing in real property investments, whether property, notes, tax liens, or leases requires a THOROUGH understanding of all LEGAL aspects concerning real estate law in general and the investment in particular.It’s IMPOSSIBLE for someone who hasn’t accumulated either a legal education in real estate law or 20 years active experience to have the knowledge and understanding of legal aspects sufficient to reduce legal risk to an acceptable level when investing directly in tax liens, notes or real property.  

Now that I am retired, I am eager to: 1) Gain hands-on experience in flipping homes in Florida, 2) Find properties with potential for value-add/forced appreciation, 3) Partner with experienced home flippers for collaborative projects.

This is my first investment property and was wondering if anyone can provide some guidance on winterizing a home.

I’ll prioritize continuing my search for distressed and discounted properties, avoiding those areas you mentioned! 

@Rick Albert is right on and gives good advice.I'm actually wholesaling a property this week, but this just happens because I am in the game doing flips, developments, and rentals. i would never try to make a business out of it. 

In what areas would you recommend I buy my first rental property?

I also have a separate mortgage account for each property.

I am hearing from a number of sellers (mostly developers) who are clearly being forwarded copy and paste emails from buyer agents evidenced by questions that aren't even relevant to the properties they are selling.