We plan to still use an agent for our purchase and let them handle that side of the transaction. 

I also handled the sale as the listing agent.

We have a property manager who handles cleaning, yard, and pools for a flat fee each month.

Lots of details here to consider so when you say how would I draft this up - there is a lot to consider but my thoughts:Rent = 1200/month3 yr option to purchase = $240,000not sure what state you are in but propose to handle everything (maintenance, repairs, etc and if that is not legal/possible you could do a Land contract or contract for deed with a  minor risk since he has an underlying mortgage).feel free to reach out and schedule a  call. seems like you have a fascinating one. 

The Sellers are retiring and the common sense kind of people - they run the operations and let professionals handle taxes, bookeeping, legal, etc.

Talk to a local independent insurance agent to learn more about how it is handled by the companies that are in your area. 

I'd be interested to know how the gift of a rental property is handled. 

We are a start-up business and still learing to handle things.

They do have some restrictions like using a certified contractor and sometimes needing a “renovation consultant” but the benefits still probably outweigh the costs especially if you already found out you can’t handle the renovation yourself.

They are also the dept that handles Helocs.