As an example, we decided to replace the windows in a house we were renovating and ended up costing us $50,000 extra because we got into issues with permitting and suddenly found ourselves having to hire an architect, speciality contractors, etc.  

How can I correct cashflow issues if I have 3 properties?

This health issue ultimately led to a close family member passing and now I don't believe they have any family living in our area anymore.2.

It is what is left after snow removal, cutting the grass, utilities, tenant issues, parking lot issues, property taxes, mortgage payment, etc. that make a difference.

I just learned that builders risk and liability insurance coverage can cease once a CO is issued for a new build.

I understand this is not a requirement, but I have never received a damaged unit from an inherited tenant or any legal issues.

Most STR markets have seasonality, and there are untold issues in the future that will effect cashflow. 

Since the properties are in New York you have a few extra steps you need to do to keep all of your funds out of NYs hands at closing.Here's an interesting BP thread on the South Carolina property tax issue you mentioned. https://www.biggerpockets.com/forums/725/topics/604427-south.... 

My manger does this all the time.He has an inspection done to verify all the maintenance issue and has someone video the property to verify all the marketing issues.

Redlining IMO would only be an issue if @Jimmy O'Connor said to stay away or refuse to do business somewhere; he did not do that, he just pointed out property characteristics.