We are having a hard time coming to a consensus of how to identify, underwrite, and basically take the jump. ( we don't want to screw it up lol) I've searched this topic on the forums but figured someone could give some insights given our situation.

As the 3rd largest MSA in the country it's hard to generalize the Chicago market as it's actually over 100 different submarkets when counting the 78 communities in Chicago property and then adding in the various suburbs, including in and around Naperville. 

The ability to speak the hard truth with empathyIt doesn't matter how good a mentor is: if they don't mesh with you personally, it will be a disaster.

.: @Jonathan Greene1. make 1 seller finance offer a month.2. do at least 1 BRRRR.3. think hard about how much to invest in other asset classes.What other asset classes are on the table for consideration?

Make sure to have your contractor ready and your cash or hard money loan ready as well to work on your repairs. 

Social media is relying on reach.Unless you have huge following,  it is hard to get traction in a reasonable amount of time.

Depends on the lender.If it has yet to go to foreclosure and you are trying to buy it prior or at sale - the answer is a hard no. 

Hard Money How did you add value to the deal?

Yep for one especially in the early stages a hard credit pull would not be useful, just have them do soft checks for the time being and opt out of credit solicitation: www.optoutprescreen.com I could be biased... that said typically working with one lender than can help regardless of where you're looking and having a relationship with that will provide the easiest and most cost effective route long term. 

Like many things, on the other side of sacrifice, discomfort, and hard work is a large financial reward.