I can definitely enter other markets, it's just gonna take some extra digging and research to find the good ones to work with. 

Just added this to my lease - thanks guys!

The property I am submitting on this week has a hot tub,  sauna, and beautiful view.I will be adding ac, EV charger, foosball table, table tennis, billiards.  

I allow pets and charge a pet rent of $35 a month, its nice bit of extra money and pet owners tend to stay longer as tenants.

The inspections have become so nitpicky over purely cosmetic items there has to be an extra $1-2k per year to keep up with the punch list every 1-2 years.

Additional escrow may be added for security for the seller.

We also require that we be added to the contractor's insurance as Additionally Insured, so we're covered if they cause damage or liability issue.3) If the property is occupied:- One of our people MUST accompany their person (and we charge for this). --- We were sued many years ago, along with the owner, because tenant claimed owner's contractor sexually assaulted them!

If anyone is interested, DM me for the complete study....Eric Do you manage STR's ad MTR's in the area?

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing.