So definitely make sure to sign a new lease (ie. your lease) even if you take over an existing tenant.  

We are in many of not most markets near or at all time record low's of existing inventory being put onto market for availability.

Also check to see what kind of third-party management companies exist in the area. 

Here is the summary if you are interested.In this case, the main question is when did the investor completed his start-up phase and became actively engaged in his business.Whether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business: (1) whether the taxpayer undertook the activity intending to earn a profit; (2) whether the taxpayer is regularly and actively involved in the activity; and (3) whether the taxpayer's activity has actually commenced.

Recently though I have come across a major FLAW in their system, which I honestly cannot believe exists: When a payment series ends, the system archives the series on the day it ends.

The deal involves buying an existing single-family house for $700k that conveys with a vacant lot.

If YouTube had existed back then, he would be a Grant Cardone of the times.

Just make sure you have enough insurance, just in case someone gets hurt.And your existing roof looks pretty good, so I'm assuming you're replacing the roof due to leaks. 

Chicago feels to be saturated and over priced, not finding great deals, but I could be wrong? 

I did not know marijuana smoke detectors existed.