Do you feel comfortable managing the project in your own? 

I'd be careful doing this, and I'd recommend trying to find some more separation possibilities within the house if you're not comfortable. 

Because I read an AirDNA report that listed it as a top location in Illinois for AirBnB rentals but I'll feel more comfortable with getting more specific insights from STR landlords operating in the area.

If that’s not an option you’re comfortable with, pay the couple hundred dollars to have a professional photographer/videographer grab the walk-through so you have it as a permanent going forward.

Since you’ve offered the $300.00, honor it.Notify them that moving forward you will not be able to provide any further rent credits and offer to break the lease if they feel the living arrangements are no longer working for them.If you feel the above is something you are not comfortable with, I wish you the best of luck with tenants that’s will drain you while they occupy your premises. 

I would not recommend buying any property you wouldn’t feel comfortable living in.

I would highly suggest getting into a market you at least somewhat know, are comfortable with, and/or have some sort of tie to. 

This might make it sound like he was a bad guy, but I think he was just trying to be an okay neighbor....He was kind of straddling that line of not doing what his agreement with the complex was asking him to do...Jon Taffer of Bar Rescue always says that people get comfortable with a discount because they come to expect it, and then get pissed when it gets taken away.

You can become more comfortable with confrontation and more successful at it.

Tell guests your new and that you want them to feel comfortable.