Improvement costs won't increase a whole lot considering I called up some favors. 

It looks like housing prices are more favorable for investing in the outer areas like Winchester vs. parts of NOVA closer to Washington DC.

Nightmare in motion is what I see for you. 

We favor people who have a history of good long term tenancies and/or seem likely they will be renting long term.

Don't give too much extended time or favors.

Based on some friends who have invested in the south shore  Chicago, I think there are a lot of positive factors working in the favor of the area.

Yes it is a good place to buy and hold and yes the rules are in favor of the landlord, but not to the extreme that this article depicts.

Its usually met quite favorably. 

We have since had renovation crews in to add 2br/1ba in the attic, which our anticipated appraisal after construction came back very favorable to the investment, due to it improving it's functionality and improving it's comparables zone.  

Much of it is from lenders trying to refi to terms that do not favor us but get them paid a few points for restructuring our debt.We are not doctors, lawyers, or any other professional that justifies this debt.