My insurance company was very receptive to adding my property management and there have been no issues since, so my recommendation is to not sweat it too much.  

its started with de Santis in FLA  signing in the new law and allowing a Sheriff like Sheriff Grady to go knock some heads and believe me they will in FLA . finally some law and order :)  GA is on the cusp of signing the same type of legislation.. the real issues is the states we know to be Tenant friendly . 

I don't see any issues with that area. 

The issue is that these loans undergo significant underwriting and can take up to 60 days to close which most sellers may not tolerate. 

Then there is the wasted emotional drain and related work. 

1 thing I would say is even in Baltimore inventory can be an issue. 

Better for resale and if one bathroom has issues that need to be resolved, your tenants can use the other one while it is getting fixed.

Usually after walking through the property he is able to give me a good ball park figure of what the renovation should cost barring unforeseen issues.

You may run into issues with lenders as a family member is leasing the property out though.

That will show you are dead serious about the issue.