Greene, thanks for your response.

There are options like:Private Real Estate Funds: These allow you to remain in real estate but delegate all the management responsibilities to professionals.

Quote from @Josh Bowser: Gang - I love the back in forth on this thread and looks like this post keeps getting responses!

Hi everyone -I want to thank you for your thoughtful and insightful responses.

When an individual landlord prices their rental, they do based on what the other ones in the neighborhood have rented for. 

✅ Demonstrate that you are a good person to work with.Be responsive, transparent, and friendly.

Is it tied to changes in the market, a response to new regulations, or part of a long-term plan?

Ideally I'd like the ability to invest in individual stocks of my own choosing (fractional shares is a plus), a diverse option of index funds, and ETFs.Has anyone found a great banking option to have the most flexibility with your HSA investments?

Cost segregation and advancing depreciation has its pros and cons depending on what the individual investor's goal is.

.✔️ You’re willing to learn Chicago’s landlord-tenant laws.Consider hiring a property manager if:✔️ You have a busy schedule or don’t want landlord responsibilities.✔️ Your house hack is more than a 2-unit property and requires more oversight.✔️ You’d rather pay for peace of mind and legal compliance.Final ThoughtsIf you’re house hacking a small multi-unit (like a 2- or 3-flat) and are comfortable being hands-on, self-managing can be a great way to save money and learn the business.