Then this "food for thought"Many OOS investors set themselves up for failure because they don't truly take the time to understand:1) The Class of the NEIGHBORHOOD they are buying in - which is relative to the overall area.2) The Class of the PROPERTY they are buying - which is relative to the overall area.3) The Class of the TENANT POOL the Neighborhood & Property will attract - which is relative to the overall area.4) The Class of the CONTRACTORS that will work on their Property, given the Neighborhood location - which is relative to the overall area.5) The Class of the PROPERTY MANAGEMENT COMPANIES (PMC) that will manage their Property, given the Neighborhood location and the Tenants it will attract - which is relative to the overall area.6) That OOS property Class rankings are usually vastly different than the local market they live in.7) That a Class X NEIGHBORHOOD will have mostly Class X PROPERTIES, which will only attract Class X TENANTS, CONTRACTORS AND PMCs and deliver Class X RESULTS.8) Class A is relatively easy to manage, can even be DIY remote managed from another state.9) Class B usually also okay, but needs more attention from owner and/or PMC10) Class C can be relatively successful with a great PMC (do NOT hire the cheapest!)

The two 1 bed units on the first floor were 2 quiet old ladies with section 8.

Your ad may be misleading people to thinking that the common areas aren't shared and you are attracting renter who want a 1bd/1ba living situation with no shared areas. 

If you list at market prices it should be easy to attract tenants.  5-10% total vacancy expense is appropriate in most Chicago markets (about 1 mo every 18-24 months). 2.TheCHA.org has a lot of good info related to Section 8 vouchers. 

Any suggestions on surrounding areas that are attractive to tourists and affordable?

If you are planning on flipping the property right away, it might be a better idea to go with hard money as being a cash buyer is much more attractive in a market like this. 

You can still find some really attractive deals there and there are some major things coming to the area like Boom Supersonic, Toyota, and more. 

Round Rock has been a popular investing location for awhile because of the family friendly attractions there like Kalahari.

Did research on crime rates, schools, attractions, etc... 

We're thinking this house-hack strategy has very attractive numbers and it seems within the letter of the law.