Advantages are you can generally afford one house more easily than a multi, easier to finance, generally more sought-after and whole categories of issues are non-existent (ie noise of upstairs neighbor complaints).

Half of them are wrong, and the other half are easily misinterpreted by the non-practitioner.

Chicago is EXTREMELY neighborhood and block specific, so the data can skew quite easily. 

With some upgrades to the upstairs I could easily get $1500/mo next year as well..bringing my monthly cashflow to about $1,591.

I can see this coming around to bite you pretty easily.

Is that the kind of thing that can be cleaned up easily?

I do find that I can beat the numbers fairly easily by running the property right.

I'm in the beginning stages of building a tiny house for myself on my mom's property to eliminate rent cost for the next few years while I save to get licensed and invest in my first deals.

I have seen the zoning maps online so the R2 designation should be relatively easily determined.

This will ensure that you eliminate turnover costs and still get the raised rents that you are seeking.