In other words making the impossible possible.Goal is to be  "retired" from the regular J.O.B. market within 5 years. 

(but looks like you would for first month)...so back to your situation, which is not clean, but check your state rules and verify without the signed lease, you reverted to the month to month, so I would really document and communicate the end of June move out date (like verbal plus a follow up more formal looking letter) and prepare for the move out then and the painters, etc to come in..

While it is great to be proactive, for a standard clean deal on a 1-4 unit property, you will probably be doing a standard homeowner type residential transaction, so you may not need much advice up front that (nothing you could not find online, like here on BP, or in books mentioned here and elsewhere).What would you ask them anyway? 

Anyone know how to clean yellow brick?  

Do you know people e.g. contractors, friends/family you visit regularly in any of these locations?  

How many regular sandwich lease options have you done? 

I am hiring a property manager for my Airbnb who will also do the cleaning.

Looking to build relationships with other investors who are serious and who TAKE ACTION regularly.

Cleaners are paid by the guests, cleaning schedules can now be managed easily online, stock ordered by cleaners and delivered through Amazon to the property, and inquiries responded to, all through a little system I built.

The guys I use clean up credit, i have watched it happen for my tenant buyers.