Readers should seek professional advice.

I invested as a sophisticated investor, although I have no professional accreditations.

Networking with other investors and professionals is crucial for learning and finding opportunities.

That would probably require a professional. 

Focus on learning the basics of MTRs, including their appeal to traveling professionals and the need for furnished properties.

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

.✅ Professional Tenant Screening – Property managers have systems in place to screen applicants thoroughly, reducing the risk of bad tenants.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

Having reasonable expectations, hiring a local professional (Realtor or PM), doing your research, and doing everything right (i.e. pro photos, professional design, good renovation, proper amenities and location, etc) are the keys to success in 2025.

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

If you want to understand 5-year outlook, I'd look for multifamily construction data in your area to understand what level of new units is and will be coming online in the near future.