The next resource Dave gave me was Earl Nightingale's The Strangest Secret.

What’s considered a reasonable target for a property in a high equity growth market like this?

There are many other resources out there  

Realtors will be able to help with resources like that. 

@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 know I might be out of your area, but I’d be more than happy to share any resources or information you might need.

My wife and I have overhauled our personal budget to reflect the 'pay yourself first' approach (allocate in order: income comes in -> invest -> donate -> fixed expenses -> variable expenses -> fun $$).We are looking to see what experienced people generally recommend for a holding tank for that 'invest' allocation while we target our first real estate deal.What financial vehicles have you guys used that works well for this?

Sell the home to whoever your target tenant will be - modern, sleek, urban, renovated, bright/spacious; then sell the location - not whether they have a bank account or need a 7/11 - just that it is located to 'dining, entertainment, shopping, more.' 

Many gurus dangle their network, trainings and resources but few deliver real value.

RE Brokers in the area are a key team member as they should know the area, good rental areas, and they will be a good resource for rentals (possibly, if they deal in rentals).