I'm not saying it's impossible (there are books on the subject sold here on BP), but it is much more difficult. 

Now, if your local market is super hot it is harder to find these types of deals, but not impossible. 

While breaking even for the property may be difficult since you are residing in 1 unit, its not impossible.

This is going to make it impossible for the appraiser to come do the appraisal.

But not impossible I'm sure. 

In my experience I have witnessed and experienced people hitting home runs in areas I would not dare to work in and I know of failures where failing is almost impossible.

It's almost impossible to predict the failure of HVAC equipment.

There's a lot of different options to increase your cashflow, but I would agree in a lot of area across the country right now its nearly impossible to find good cashflow on day one just buying right off the MLS. 

There is no way to edit it on my end and airbnb refuses to edit saying they cannot do this and I have to do it myself (which is impossible) this is even after I send them the new license number and screenshots from city of chicago. 

Your question is impossible to answer without a lot more detail.You should visit the site with your architect and a builder who has experience with hillside construction.The exact lot and soil conditions will dictate the costs.