.- Use local real estate agents who are familiar with investment properties to help you find the right deals.You're taking the right steps by seeking knowledge and networking.

I like option 2 to diversify the investments in 3 smaller rental propertires, 3/2 around 1500 sqft, in good school districts which will open the biggest pool of tenants. 

Sharing experiences and pooling knowledge might uncover creative solutions you hadn’t considered.While it’s frustrating to feel unprotected, focus on taking strategic, proactive steps.

Right now just working on market knowledge in my college town.

While the initial years might not be financially lucrative, the knowledge and skills you acquire will be invaluable.

The deeper your market knowledge, the stronger your relationships with agents, contractors, and lenders, and the better your deals will get over time.

Closer to entertainment district, services and mass transit.  

.✅ 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!

Gaining knowledge about investor loans, like DSCR loans, can be particularly beneficial.

To my knowledge, guests also have trip insurance.