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.  

>Sacramento remains affordable at $1,850/month, with minimal growth.

As long as you can afford to make the repairs within the next year or so and you're not spending more than the house is worth, I would move forward with the purchase.

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?

Hard Money Loans.There are other niche products but those are also in general order of cheapest down payments and interest rates typically.Good luck!

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. 

So, average cash flow is a product of the choices you make and the capital you have to deploy, as well as your lendability.I think what @Alecia Loveless wrote should be very helpful to you in terms of judging the money coming in, but it all depends on your location and investments.

Can you afford the downpayment, brrr costs, keep money in the deal and have sufficient reserves for both properties(i.e 2 years of vacancy/lead times, 75-100% of capex, 3-6 months of random ********?

And buyers simply cannot afford to add to their DTI due to the lack of affordability and looming employment issues over our head.No one will sell, unless they are forced to.

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.