It is an area you are likely more familiar with and closer to which could be helpful for your first investment and as @Sarah Kensinger metioned, you may be able to do a MTR.  

Rentredi seems to do it all but the reviews for it say there are a lot of bugs and a lot of hidden fees.

I just know I don’t have the knowledge yet to find a deal and a lower price point is appealing for sure.

It's a lot of work upfront but once the team and systems are established it gets easier and as you get better you can expand to another city. 

I have a pretty straight forward return with a W-2 and a K-1 from an LLC. 

These are professionals with additional training and a stricter code of ethics.

Just kidding (sort of).A lawsuit will cost you $25,000 to $125,000 and a year and a half of your life.

I'm in South Loop near the Loop, lake, Grant Park, CTA, and a variety of hospitals / schools, so renting out the room on a mid-term basis (32+ days) for a premium was the best strategy for me.

I feel bad for the pitbulls, they need to go somewhere but the owners also need to be responsible with them and as long as you make that clear then you shouldn't have a problem.

In this manual (which I assume could be modified to provide to tenants) I include all the financing information (which you would not include for tenants) bank accounts, mortgage accounts, payment information, and mortgage payoff), a list of the contractors, what each contractor does, a list of upcoming planned or necessary repairs, and a copy of all leases associated with the property.