The areas where I forecast the strongest future growth are Rogers Park, Albany Park and Portage Park.

So weather you have a mortgage or not, you are paying that fee.  

Hows the weather up there in Watertown?

Insurance, weather related events, and labor costs for cleaning have been a big cost this year for  us.

I would not anticipate much turnover so could be good cash flow over the long run, the question is the long-term appreciation… depends on your strategy and weather you’d be managing themselves or relying on unknown local property manager, contractors, etc.

what is important to you - city, suburbs, weather, sports?

And it certainly has nothing to do with the "horrendous" weather. 

I would not invest if the good guys are losing ground, but that would run counter to your description that it is an appreciating area.It looks fine to invest in for the information you shared if the long term forecast for the area is safe and stable to improving.

I do not need a big pitch deck put together - if I need more info I will ask for it but typically first thing I ask for is the proforma - what are the assumptions and review them to make sure they are realistic.Saw a deal about six months where the rents were $600 and they were forecasting $750.  

Renting in Dec or January is orders on magnitude harder than in the summer even in mild weather San Diego.