@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.

I met this real estate agent on facebook, seems very active within the real estate community in that particular area based on the posts she's engaged with. 

You can cold call, door knock, do social media ads, mailers, network, etc.

The rules are designed to prevent related parties from engaging in exchanges that shift high basis property for low basis property, followed by a sale of the low basis property, effectively "cashing out" without recognizing gain.If you sell a property to a related party as part of a 1031 exchange, both you and the related party must hold the exchanged properties for at least two years following the exchange.

No social or credit pull needed upfront. 

I am new to Bigger Pockets and looking for opportunities to engage, discuss, and work with others in the field of REI.

There has always been many questions as to if one needs to be licensed to engage in COMMERCIAL mortgage brokering/origination or RESIDENTIAL INVESTMENT property mortgages.  

We gave him 56k in deposits and he will not even pick up his phone or engage in a conversation.

When parents employ their minor child, the child is exempt from Social Security and Medicare (aka FICA) - if under 18.

This straightforward process allows you to verify encumbrances before considering a property investment.Alternatively, engaging a title company can offer a more comprehensive approach to uncovering liens.