This is a key element of the process, where they can learn all they need to about there options and choose the best one, which may or may not be a LO.

No greater waste of time for a LO than to ask a self employed person how much they make.

Bought a second home/primary residence in Tierra Verde, FL about 3 months ago and was planning to do STR May-Oct (6 Months) and live in it myself Nov-April.  

When I bought a two flat in Chicago, our lender was satisfied with a LOE stating funds ($25k) were gifts to my wife and I (12,500 each). 

It appears you are talking about a Land Contract, not a LO. 

A vacant lot in a poor has really No. aloe....the cost to build something would be more than double what surrounding properties are worth, so it’d make no sense.Also, eBay is where most buyers of tax default junker properties attempt to unload them on someone.

What contracts do I need with the Seller in order to be able to do a LO or Contract for Deed with new tenant/Buyer?

Despite being a LO for a local Hard Money lender, I'm always looking to get more knowledge and insight under my belt and love meeting new people interested in real estate.

I've never done a LO before, which is why I'm asking what common approaches experienced investors use.  

If I want to do a LO, as does another party, it's none of the states G**am business IMO.