If you get your system and modeling down and follow what I mentioned above with respect to coming up with your strike price/offer price, you shouldn't look back if someone overpays for the property.

Having local family gave me a built-in support system, market familiarity, and the confidence to manage a property from a distance if needed.

I completely understand all the financial calculations and models in the system and yes, it would have been fairly easy to build one myself, but very time consuming.  

Management & Automation: For those managing remotely, what tools, software, or systems do you rely on?

.✅ 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!

Stessa is really an awesome system.

Also, how much does it cost to get set up on this patented software system?

I strongly advise anyone purchasing an old house to flip to ensure they have a clear understanding of the condition of the home's drainage system.

My suggestions:* Requiring code compliance and safety equipment is absolutely valid and should be part of the regulations* Requiring owners live within 15 miles is not necessary since poor hosts whether they're local or distant will violate the 3-5 warning system and earn a suspension.

Our company is actually starting an Asset Management Mastermind to address these infrastructure issues and share our systems and procedures.