I've seen a lot of talk about house hacking and while I believe that I understand the list of it, I'm just not confident to start.

Give it a read, and you'll have a fair understanding of the process. 

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

Your goal is to build a passive real estate portfolio (we can discuss what passive means to you), so while I don't condone throwing $100k into a deal without even a basic understanding, alternatively doing so will teach you far more lessons than reading a book will.  

I would look for an experienced agent of my own who understands what is standard for your market.

Hey Joseph, my understanding is that if you wanted to team up with an accredited investor though an LLC in order to invest, both members of the LLC would have to be accredited.

Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

I am starting with a small budget(100k-120k) so trying to understand which neighborhoods I should focus on, would love to get recommendations if you have :) I live south of the city and only like to go about 30 minutes away from home. 

@Jerry Chilimidos I am not a CPA owever my understanding is any loans to your IRA can not be personally guaranteed.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.