I would add to this account every month, allowing me to pull from it whenever there was a large repair or capex event. 

@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.

If you’re looking to invest in your backyard, it helps to network with as many locals in the industry as you can.

Using these parts of local zoning can lead to potential deals.  

In one case they used a notary at the local US consulate.

We're also seeking to buy a local (Raleigh / Durham) property management company to expand that business more rapidly.

I am new to real estate investing and looking to connect with any local investor.Thank you!

I think you should explore local and non-local CPAs before making a decision.

Find them at local real estate meetups, but be careful, it's a sketchy business overall.

Ensure the property’s price aligns with market trends, and work with a local realtor to help with due diligence and negotiation.Good luck!