Not 100% sure if Gates applies here, because nothing would be added to the formerly residential land, only removed from it.

Tax advantagesAlso, I think if you link up with the right Chicago realtor and team you can find something to make some money right out of the gate on. 

We still needed to repair a fence gate, which we did while they started unpacking.OH, that cleaning person, and handyman, well they were not available on Sunday night (literally all night) on a holiday weekend.Another move out, an elderly man was moving and had packed up a POD, still had 2 more planned. 

Security- $50,000; motorized gate $20,000g. 

Ideally, create a separate gate to be used just by the ADU tenant to access their unit.Natural light: ADUs are small and one of the best ways to make these spaces feel bigger is to ensure lots of natural light is flowing into the unit.

After close we're investing in a new automatic gate, management software, and automated unit entry systems to start.I have a family friend we're working with for private-money type financing, but does anyone else have another solid financing partner for this type of project?

Nathan,     To your first point, I have two years of rent equivalency saved in reserves for this property; we replaced the roof two years ago, all appliances except the fridge are new or refurbished, the water heater has been replaced and the fence/gates mended from a tornado.

A fellow contacted me asking if the rental I listed was in a gated community or had 24 hour surveillance.

Is the facility gated / fenced? 

Added exterior security gate, painted exterior, purchased new ss appliances.