I would like to retain primary ownership in the property.

People losing their homes had zero desire to move back in to an apartment.We offer 2-3x the space, garages, yards, no shared walls/fellow tenant drama, and in home laundry for a few hundred more than an apartment and less than ownership costs for the people that only put down 3% on a 6% loan. 

I am not an expert to maybe you should consult with lawyer and accountant but if its sole-ownership LLC, it doest not really matter for tax purpose if you are filing schedule E. 

It's important to know what options you have, and which ones you don't have.Ultimately, if the cash for keys doesn't work (and it may not in this case because you'd probably have to offer him a lot of cash to offset the benefit of him living completely rent free), then you may just have to wholesale this deal at a steep discount and let the end buyer deal with the problem and evict the tenant once they take ownership. 

I will be selling my ownership in one of my companies for $300k.

First, favorable premium rates are given to homeowners for the inherit “pride of ownership” that comes with personally occupying a home.The second reason is that when a property is vacant, it is much more vulnerable and likely to have what the insurance world calls Vandalism and Malicious Mischief (VMM).

This may be a better resource for youhttp://www.dglandlord.com/We are committed to helping independent property owners with 10 or more Dollar General stores to achieve improved financial results and reduced complexity of ownership as a Landlord.

And then if I really wanted to dive into one of the principles that the book offered then I could go purchase the entire book.For example I'm reading Jockos book on the extreme ownership. 

If you mange to buy 1 good deal a year you are doing well. but of course you can do better if you put more time in to it.The LLC would come in to the play at the stage when you close on the deal, OR after you took ownership. some lenders (conventional 2-4 mainly) would allow LLC ownership. -- seek legal advise.

The option costs you $5000, and the Option Agreement states that the owner of the Option agreement has the right to buy the property for $100k, within a 3 year period starting from the date the OA was signed.2 - You then sell that same Option Agreement to the end buyer for $10k...which then gives the end buyer ownership of the option Agreement, and the terms within that agreement.3 - The End Buyer now has ownership of the rights you had when you owned the Option Agreement.4 - You made $5k on the spread between what you paid for the option originally, and what you sold that agreement to the end buyer for.5 - The current owner/seller of the property has no idea what took place between you and the end buyer.