I may focus on that market since I can hit some people up to be boots on the ground. 

Boots on the ground is hyperlocal, and what you're looking for is essentially cheap labor that can open a door when you need it.

Find something with someone who is boots on the ground, that you have talked to and built trust. 

Regarding next steps, I agree that the best way to approach this would be to have one person act as boots on the ground and the other person handle the back office related items.

To combat this: market the property well, be transparent, secure a great flood insurance rate so a buyer can know the cost and be able to transfer the policy.5) no flood zone AE does nothing to rental rates6) if the insurance rate seems high then get a flood cert and maybe it will decrease.

Boots on the ground, or lack thereof, are where the mistakes are made.

My biggest concern is just having boots on the ground in case something goes wrong.   

For example one person could manage paperwork and another person could be boots on the ground.

Doable if you lean on local boots-on-the-ground (realtors, PMs) and avoid another Cahokia overprice trap.

Escalation clause is an attempt to combat that potential lie.