Would love to get second look over my assumptions, challenge/reveal any flaws in my current plan, and listen to any suggestions to successfully house hack in Austin, TX.Main Goal: House hack to live for free, cash-flow ~$150-200, have the ability to cash flow some after I plan to move out in a few years.My situation: Newbie and aspiring real estate investor looking to purchase my first deal at the end of 2020 (Ideally November/December).

How capitalized are you (what is your ability to absorb big expenses if/when you have them like a major capex event)?

The other side to buying in almost all of CA right now is that evictions are not possible by any means, never mind rent control on top of it, but if you are adopting tenants in a 4 unit its not likely going to cash flow, and unless you have the ability to do cash for keys, and you have tenants willing to move then its another hurdle to cross. 

@Ry Eikleberry, The most critical component of success in any venture (and real estate is no exception) is your ability to draw a team around you. 

Even having a couple backup plans would help tremendously & increase your ability to make the best offer for you. 

I would start with your own ability to close first.

Do you host with AirBNB because of their fees and policies or their ability to get your unit rented?

So cap rates can be higher in the Chicagoland area, but you still have an ability to find new tenants if someone moves out... this is different from other markets which sell between $50-150/SF where you have significantly lower populations, so there are limited new renters in some markets.

I have confidence in my ability to do everything necessary with the exception of getting a loan. 

At the same time, the new regulations allow for the ability to put the money back into another pre-tax account like the SDIRA.