@AJ Smith you can reach out to any of us that are investors or realtors here on BP and we can help you tighten up your understanding of the Chicago market.

Insurance carriers are really tightening their restrictions this year so I think it is unlikely you will get a comprehensive insurance policy (RCV) without a roof replacement. 

Before you decide to convert it into a sfh, double check the comps around your property.If the straining surrounding houses are duplex, or multi units, converting yours into a sfh may not be attractive.

The turbulence in the mortgage market has caused many HMLs to tighten their requirements.

Tightened up a few loose screws.

I’ve tightened up my strategy since then.

As the market tightens you may find it harder to meet your criteria, but unless you're being really unreasonable (and your agent will tell you, if you are) then you're probably wise to stick to your guns.

As a family investor in Oakland, at the present moment the Mayor and Council are considering tightening rent control considerably, including forcing owner-occupied units to be subject to rent control.

The strain from the high cost of capital for businesses and consumers alike will be too much.

This will allow more particles through but will cause less strain on the machine and make it more efficient.