Everyone seems to talk about including the costs of the new mortgage, taxes, insurance, maintenance & capital reserves, and the vacancy projections when looking at realistic cashflow, which we already do for all the properties in our rental portfolio.But we, like many, cant find properties that are making any cashflow sense right now.

Now I'm left wondering whether it's best to lower the price to get the property off my hands asap or to make some costly improvements that will probably neutralize any increase in value.

The potential risk you're taking on is not worth the cost savings IMO. 

Main reason is what if someone needs 2 weeks?  

Essentially the reason I was successful in my first year of real estate was not reinventing any wheels.

I realize they must have done this and think this is likely the reason they have not inquired about the security deposit.

My properties are listed on both, but I keep spreadsheets on "issues" their resolution and how much it cost to resolve them. 

Finally, closing costs were reasonable.Cons-  Quality control of closing docs. 

We have been through 3 contractors at this point. 2 backed out due to the way the payment works on this loan and one didn't give a reason just stopped responding.

I’ve requested financial statements, tax history, utility costs, and information on the property management company.