I really want to get a local, first-hand homeowner with some experience to talk me through the complicated flood and wind insurance that is required down here.

I know it's a complicated question.

In my experience, entering into those side agreements can only complicate things. 

Forget about the complicated stuff like cap rates, which aren't really used on single family, and definitely don't buy hoping for appreciation.  

AaronForeclosure in MA can be complicated.

From the intricate details of your design to budget complications, getting it right requires effective communication.

It sounds like a very complicated thing, dealing with lawyers or estate managers, blah blah blah.

My parents are working on closing a complicated conservation easement on the family ranch out of state. 

It's not really that complicated: Whole House: ADownstairs: BUpstairs: CA has B&C calendars syncedB has A calendar synced (not C)C has A calendar synced (not B)When a reservation is made on A it blocks the dates on both B and CWhen a reservation is made on B it blocks the dates on A which in turn block them on CWhen a reservation is made on C it blocks the dates on A which in turn block them on CIf you sync B's calendar to C and vice versa, a reservation on B would block C which is not what you'd want

This leads newbies to chasing loan investments with greater degree of risk which often leads to loss or at least unnecessary risk.