House hacking in Chicago can be a game-changer—letting you live for free (or close to it) while building wealth through real estate.

Paid-in-full real estate almost always results in sub-optimal returns.Do this math. 

I started my real estate adventure by purchasing 2 single family houses in Oklahoma with 2 cousins, mistake #1.

Today its difficult at 20-40% down to make something cash flow (in real life not on paper).

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Connecting with local GC groups in your area will help you connect with subcontractors, find out tips and tricks of the trade in your local area (since all areas and their real estate differ slightly).Also, have you considered the motivation behind building a brand-new duplex versus finding one on the market?

Consult a tax professional to optimize deductions and explore strategies like Real Estate Professional Status or short-term rental loopholes to apply depreciation to non-passive income.This post does not create a CPA-Client relationship.

Just real, on-the-ground strategies.

Personally if you are looking to grow in real estate going the traditional method/way of getting good properties under agreement with traditional financing will get you to where you want to go faster than trying to find all the needles in a haystack.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?