Additionally, with the City adopting the IBC 2015 and inspectors becoming increasingly difficult to work with, we've labor costs go up and soft cost on the design & engineering side go up as well.   

I worry about city/government restrictions on short term rentals, but am not familiar with current laws in Chicago.

Walk area on google street view. look for bars on windows, what type of retail? 

It turns out that on his lot is also an old parking structure (street fronting) that has been fully permitted to build a 1000 square feet townhome (the final map will son be recorded). 

A very similar 4 plex down the street is was listed for $449,000 and is pending now.

Is this particular property within Seattle city limits?

I recently acquired a duplex in Sacramento, close to Sac City College.

Too far away from the local college for walking (approximately 3 miles) and the property is located in a different city as the college which has a poor reputation. 

Here need talk to building department for address change. depend on city, some are easy some are difficult.BTW, in some Asian culture, 666 is super good lucky number.

Unless the house is worth more than 75K arv, almost no banks will refinance you out in Baltimore City.