The regulations in Chicago can be quite overwhelming, so I’m looking forward to exploring the opportunities in this area. 

This may seem like obvious advice, but I'd say just get three or four quotes before settling. 

For the flip itself, this would mean a GC or better yet, have a crew there that can handle 60-70% of all the work meaning they are there working on it the day you close and stay there throughout the process till it's completed. 

@Randall Ayers By coincidence I was at a market update meeting this afternoon and a presenter was a hard money lender in Arizona and...wait for it...Colorado.

This is probably something you should just add to the rent for your next tenant.  

@Elton Tate is this a single unit or duplex?

Again this has to do with YOU and how YOU run your property.

This will clarify and reinforce what you are reading.

Your test ad doesn't mean this house is a great STR.

Like you, i'd be interested if anyone here has any experience with doing this 'technique'.