That said, I will be replacing the exterior siding with probably engineered product...the current siding is attached right to the studs no sheathing, so I will have access to the walls from the outside. 

North Side?

Like a brat, I remember tossing a package of hot dogs in the flower bed outside my front door. lolThe fridge/freezer was ancient but they did correctly repair it. 

We will be living in one side and renting out the other.  

I stay on more on the SC side.

I've been looking around Chicago, mostly on the North and West side.

Time is proving that this is probably a little on the heavy side, but I'm going to keep it at that level and accumulate the cash and await other opportunities.  

Wow, thanks for the insight Jennifer, getting an actual scenario on the numbers really help understand which side of the wind is blowing.

I was amazed at how well it works,” said Webb, whose rental rates range from $99 to $225 a night.During peak season, Airbnb hosts tend to raise their rates much like hotels do.Lupita Johnston, who’s been hosting since 2014, charges $300 a night during the gem show — more than double her usual $120 rate — but her guests don’t mind, she said.For roughly the cost of two queen beds at a four-star hotel during the gem show, Johnston’s guests get a 2,000-square-foot west-side house filled with art and antiques, with mountain views and sleeping space for nine people.Visitors come from around the globe, she said, rhyming off a list: “Panama, Holland, Germany, India, Japan, Finland, Denmark and all over the United States.

The fact they are complaining online might be an indication the property manager dealt with them properly so be sure to ask the manager for their side of the story.I hope this basic guide helps.