When acquired, the property was mismanaged, there were tenant issues, deferred maintenance, and was rented at below-market rates.

I have a issue in which I can hopefully get some good feedback for a flip in Washington, DC.

I'm guessing when all is said and done it will cost around $100k for the conversion, perhaps a bit more should I run into issues with rock in the ground when running utilities.

Then there’s also accountants, attorneys, and credit repair specialists who work with individuals with issues that prevent them from getting a mortgage. 

Pigtown has some incentives associated with it from some local companies such as UMMC however I really see this area taking awhile to develop and some of the people I know who have purchased there regret it due to safety issues. 

I have been managing "per cleaning visit" electronic payments to cleaning company for several AirBnB properties for a few months without issues. 

That seems to be the big issue.

But in your post I keep coming back to two issues.1.

You don't want to find costly issues after closing that a home inspector could have easily identified. 

If that is the only issue I would rent to them (depending on the type of home etc.)