Anyone in OUR situation (who is not in the 1% of 1% and has dividend / investment income that would provide a sufficient means of living otherwise) is going to be totally focused on cash-flow.  

But don't think I'd sleep at night if I did.

It's sleeping with the enemy part 2.

My opinion reviews your financial situation first because jumping into real estate or real estate investment you will need at least six months of reserves financially self-sufficient to support yourself.

Effectively buying at 100% CLT with a 1st position portfolio or DSCR loan combined with a seller 2nd that the lender wouldn't otherwise approve....It sounds like this is a recipe for getting sued at best, and arrested if it rose to a sufficiently large scale where charges were brought against someone.

Only problem, they didn't do their homework, this wasn't an area where that sort of thing is actually sufficiently in demand to support that restaurant, at the prices they needed to turn a profit.

To make broad generalizations or assumptions about entire quadrants of the city being "problem areas" is an error in judgement, in my opinion.Now, there are areas on the west side that I definitely try to avoid, but if I have to go there, I make sure to do it in the morning hours when most of the delinquents are sleeping. 

You are a landlord and have to treat it as such.Insurance and taxes typically only go up, so make provision in your lease agreement to make sure that the lease payment is sufficient to cover the probable increase.

I could rationalize it's for my long-term investment in the property and still sleep okay if it's the right thing to do.  

but once a policy is in place and there is sufficient cash value then credit is of no concern and it's yours to leverage how you see fit.As for the $20k that can absolutely be sufficient to flip a property or help flip a property.