Dee Jay Chicago has quite a few issues and property tax increases seem to be one of their favorite ways to solve them.In a city like that I would also be afraid of regulatory hindrances like rent control and the city just not being landlord friendly in general.

(Not everyone qualifies for the 401k)There's much misconception regarding the role of custodians and administrators, as well as the extent to which they should be relied on for advisory services.There are many excellent companies, but as the number of custodians/administrators has swelled it has become increasingly difficult to navigate the space.

So after a few months I'm looking to increase the rents and locking into a 12 lease or find new tenants and refresh the property.

After the renovation, we expect rents to increase approximately $300.

Most zoning allow for 2-4 unit You rehab cost may increase but so will you rental income

Rather than a principal only payment, I did a recast after 12 months which increased my cash flow due to the new amortization. 

I increased my rehab cost to include the holding costs you mentioned.  

Our market has seen a lot of appreciation but I’m seeing a current cooling with longer days on market and an increase in price reductions.

Unless you're planning on significant appreciation or rent increases this is likely a loser, although ultimately I would decide based on the potential internal rate of return for the duration of the investment, to see whether you can invest that money for a better return elsewhere.    

The closer you get to Boston, the more you are competing from an investor standpoint with investors who are seeking portfolio diversification and appreciation -- both of which increases costs.In my opinion it comes down to you what you're looking for.