The best market is likely a "Good" cash flow market that you have some ties to, in some way shape or form, or one that is a reasonable drive from where you live, if practical/possible. 

My bank account is connected to Stessa to eliminate the need for me to manually track income, expenses etc. 

No reason for me to go the through the hassle of the sale process unless there is some type of gain which the investor is open to and this is where I need the advice.

In real estate, I don't change locks, screen tenants, evict tenants, inspect properties, or finance my deals - I have property management, property inspectors, and mortgage lenders that do this for me (outsourcing).

Feel free to message me if you want to dive deeper—I’d be happy to share what’s worked for me!

You could look into forming a C Corp as an alternative way to own this property that could affect your tax returns differently, I am not a CPA or giving tax advise.

I appreciate any feedback.Regarding Insurance, personally I would never have someone else (A Lawyer) handle the insurance on a Sub 2 deal or any other real estate deal for me, you would be setting yourself up for failure.First of all now you would need to get a POA for the attorney from the seller, that may not be your best move.

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.

For me, being an agent makes it so much easier, because all we can do is disclose disclose disclose. 

And i found launch control but the minimum is $500 a month, but they use cross-referencing data across sources to find the most accurate contact information by using a person's name and address to find their phone number, real address and email by accessing public databases, phone number directories, credit reports, utility bils, public tax records, and social media profiles. this is waaay expensive for me as a beginner. what do you suggest or if anyone has any suggestion I'd greatly appreciate it.??