However, your property manager should be able to guide you on legal options and solutions to secure the property and possibly help with claims for damages.

Mom and Pop shops are not that great at accounting and the numbers tend to look like they can't afford to live so take that in to account plus the operations they are doing. 

He's the CEO of a company that builds healthcare facilities, and you rented him a "fully furnished luxury executive rental," but then you said he's broke and couldn't afford to give his kids Christmas presents?

I’m stating to look around some of the smaller markets outside of Boston, starting to dive deeper into market research to see if some of the more affordable areas are sustainable for rentals.  

They have a mix of solid rental demand and still offer relatively affordable entry points.FWIW, those aren't areas I specifically invest in today but they will give you some anchors and are examples of strong neighborhoods.As for schools, it’s true they can be a challenge in a lot of Detroit.

These are real human beings in bad situation and they need real advice and real creative solutions to get out from under it.

Or other solutions we should consider?

For example:Tenant ManagementLease Automation & E-SignaturesOnline Rent PaymentsTenant ScreeningMaintenance Request TrackingMarket Vacant PropertiesIncome & Expense Tracking (Do you use QuickBooks and want to continue, or does your current PMS have its own solution?)

If your local law allows it, see what everyone else is doing and go by the norm. 3 months rent is a substantial amount for some, but really helps ensure the financial quality of a tenant.Sometimes I have immigrants who apply who work their tails off and can't afford the 3 months up front.

I do not necessarily agree with these solutions, although I am open to the argument that they may be effective.