If you look at other threads on the Chicago market this topic comes up a lot! 

The one thing I can say is that if you go downtown to the city of Chicago, you can get to talk to someone which is quite helpful.I ended up getting my operator's license which actually wasn't as challenging as I thought it would be (I went downtown to get it), but didn't end up using it because our airbnb also got denied lol because it was in a "planned development area".I believe there were a lot of neighborhood complaints about airbnbs so that is why they are putting such strict stipulations around 1-4 unit builds.  

I'm a bit confused on how a good listing broker could net me more when I'm already at the top of the market.

I don't know if there is an "ideal real estate market" these days.

What market?  

I ran some numbers on a few markets and I find I can cash flow 500+ with my 100% LTV method.

. +30% vacancy for 24 months, caused by two evictions, one unit on market for 7 months, and the two new properties taking 1 year in renovations instead of 4 month estimate (~$30k of lost income above assumption of 10%)2. $45k from several unexpected large repairs (water leaks, roof collapse, siding rot, plumbing main line, etc.)These issues are also causing me to rethink the assumptions in my model, increasing my vacancy rate from 8% to 12%, repairs from 5% to 20%, and capex from 5% to 20%.

Then together take it to market depending on what that research shows and client needs.

Found this deal on market & we negotiated normally.

:texture looks weird. looks cheap, looks like florida houses looked 30 yrs ago and most of them still have that stuff on the walls.it hides imperfections, but i dont like the looks of it.I hate texture, and never use it in Atlanta (buyers don't want it)...But, in two other markets where I rehab, buyers actually EXPECT it!