Key Factors for a Good Seller-Financed DealCash Flow: Rental income should exceed monthly payments (PITI) by at least 1.25–1.5x.Purchase Price: Compare to ARV and market value for fair pricing and equity potential.Interest Rate: Aim for competitive rates; higher rates must still allow positive cash flow.Amortization/Balloon Terms: Favor longer amortization and align balloon payments with your exit strategy.Down Payment: Lower upfront costs reduce risk but should meet the seller's expectations.Flexibility: Seek no prepayment penalties and fair late-payment clauses.Property Condition: Ensure the property’s condition matches terms through inspections.Seller Motivation: Assess the seller’s willingness to negotiate favorable terms.Exit Strategy: Have a clear plan for refinancing or payoff at term end.Portfolio Fit: Ensure the deal aligns with your financial goals and risk tolerance.Vetting multiple deals and consulting professionals is crucial to making sound decisions.

Detroit is a great city to invest in one just has to be aware that is is a block by block city and to be careful

What does he care if it costs him millions?

Is it smart to just sell, pull equity to put towards the new house or use the potential rent to put towards the new home payments once the rental overhead is taken care of?

While it is possible to convert an investment property acquired through a 1031 exchange into a primary residence, this requires careful planning.

My favorite approach is attending networking events since they offer a great mix of agents and professionals. 

These days as you mention with STR almost everything can be handled remotely...cleaning, painting, locksmith, yard care, even drive by pictures of the house occasionally or internal pictures too. 

.✅ 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!

Shared housing provides affordable, flexible rental options for young professionals, remote workers, and students.As shown above, co-living properties have more demand than traditional two-bedroom units and appeal to a wider tenant base.2.

In Phoenix, where I’m based, or in markets like San Antonio, the best realtors do more than just list properties.. they go “driving for dollars” to find oppurtunity, leverage their local networks (probate attorneys, CPAs, divorce attorneys) and carefully analyze each property’s cash flow.