You're dealing with your "bad apple" that will forever help you curate your search criteria whenever you place future tenants. 

I can contribute $1 less to MBDR in favor of after tax, which is widely considered a good idea, but withdrawing $1 of Roth basis and investing it after tax is a bad idea?

If you have reduced the risk as much as practical, feel that the potential upside is sufficient for the risk that you will take, and have the ability to bear the risk/survive a bad outcome, then it's time to take a swing.

Just make sure it is not deep in the ghetto, as there is a lot of bad areas in Cleveland.

One has a little bit of a steep driveway, but not too bad.

if you're beginning conversations with agents, and they don't recommend that you sign this agreement before the close on a property, is that a good thing or a bad thing? 

About 1/3 were in limbo--neither rebuilding nor selling, while owners tried to decide what to do--sell, rebuild, or fight with the insurance company--or just didn't have the money to rebuild and didn't want to sell. 

It could just be bad luck or improper tenant screening.  

If their deal goes bad, you could foreclose on that property and hopefully recover your funds.

If the yard is bad but everything else is move-in ready, that’s one thing.