There is still another month in planned rehab, so nothing pressing, but would love any recommendations people have!

I want to help her out but also want to avoid significant financial loss.

I'm under contract on a single family home in Chicago, and the rehab will include adding two dormers, so I'll need an architect to draft a full plan set for submittal to the City of Chicago Planning Dept.

So where does one begin if the ultimate goal is to become a financially free investor?

@Samuel Boyd I am not very familiar with the area but plan to be spending more time down there.

I'm particularly passionate about house hacking.Outside of real estate, I enjoy playing pickleball, paddleboarding, and learning about how to become financially independent.Excited to learn and connect with you all!

There are over 20+ active CPAs here in Biggerpockets assisting RE investors with their tax planning.

Don't get me wrong, I love STRs, but if your place is average, you plan to keep it average, you may be better off just getting a long term renter and make out better. 

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

My investor plans to turn this into a nice 4 bed home with the goal of selling between 250-275k What made you interested in investing in this type of deal?