Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.

I’d love to hear your thoughts on whether this approach makes sense or if there are other strategies you’d recommend to optimize profitability.Thanks in advance for your advice! 

It's  bit of a specialty approach.

@Celine Besson there will be several challenges:1) Finding a Grate Property Management Company. - See our copy & paste advice at the bottom of this response.2) Managing the Renovation- Everyone thinks a PMC can easily do this. 

I’ve developed a Comprehensive Investor Report (CIR) for a property in Palm Coast, FL, designed to be transformed into a luxury rental asset while serving as the foundation for a scalable asset management strategy.Here’s a quick snapshot of the deal:Property: Red Birch Lane, Palm Coast, FLCurrent Value: $350,000+Mortgage Balance: $165,000Current Equity: $185,000Investment Required: $177,500 (for luxury upgrades and optimization)Projected Monthly Rent: $4,500 with 2% annual increasesTarget ROI: Full 1.5x ROI for investors achieved in 9 yearsLuxury Features: Smart home automation, designer finishes, professional-grade kitchen appliances, and more.I’ve also structured a capital distribution plan with a waterfall approach:8% Preferred Return for investors.Full Return of Capital to investors before profit splits.Post-ROI, a 20/80 split (Investor/Management) ensures long-term alignment.

It's laborious, messy - but it was far less damaging/challenging than the photos found on the internet...even with plastered walls.  

Challenges?

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Isn't it unlikely that a homeowner who cant afford a 2-3k tax bill would even challenge this legally?

Reread what @Stuart Udis wrote.We can testify to the same challenges after 25 years in our marketplace.We also agree with @Kristian Sexton about starting with a PMC.