One of my friend happens to be a RE agent, landlord and a property manager himself and he seems to feel that as long as she pays rent on time and does not create nuisance, not to worry much and just keep do a quarterly property inspection.

Will finish both tomorrow then work a shed site down below and a road around the property.  

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.  

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

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

It sounds like you need a less advanced system which is totally not a bad thing, and Joe, although is awesome and a great asset to the industry, if inherently a slob-like dude, who before having success with this lease option stuff, had a "good enough" type of attitude... 

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.