A few common items such as:1.

Here's are some other common terms for House Hacking -> Room Sharing, Owner-Occupied Rental.

Eventually I want to have a go to foundation contractor as well given the fact foundation repair is so common in our area as homes age.

I used to go medium oak on the theory that if it looks like the most common hardwood floor color, it will get less scrutiny than some picture of exotic hardwood. +1 on Ben Moore Navajo White!

you dont a good agent repping a buyer is going to go to bat for them not U keep in mind many sellers lie about all sorts of things.. not saying your that way but it is common the industry.

Why will likely determine how because if you are looking for cashflow vs. appreciation vs. quick capitalHow could it be househacking, brrrr, flip, long term -> You mentioned BRRRR, which is an awesome strategy but will only work in specific sectors of Chicagoland. finding the perfect brrrr in the current environment is extremely tough!

Obviously the tenant hope of bringing in more occupants (and sharing more common area space/bathrooms as a sacrifice) would be to lower the rental cost per person.  

However, 190 days seems extreme.

The architectural quotes I have received for design, city review changes, and all construction docs are extremely high. 

As a newbie, it is easy, and common, to head down multiple paths chasing shiny bright objects, with many of those paths just leading to time wasting and increased experience in learning what you don't want to do.