Can you still find a real estate deal that works in today's market?
Housing prices are higher. Interest rates have changed. Renovation costs have increased. And if you're comparing today's opportunities to what investors could buy during the recession, it can feel like the good deals disappeared.
I thought so too.
In this episode of Rental Problems Solved, I compare real properties and actual sale prices to find out what opportunity looks like in today's market.
We look at:
• A single-family home that recently sold for $59,000
• A $525,000 two-flat and whether house hacking can still make sense
• A six-unit that sold for less than a 2-flat
• Why purchase price alone doesn't tell you whether you've found a good deal The biggest thing I discovered? The opportunity may not have disappeared, although strategies have changed.
📊 Free 1–6 Unit Deal Analysis Calculator Make a copy and use it to analyze your own deal: https://docs.google.com/spreadsheets/d/1tiyV-vkF8ITBUWfxQbGReIihef30_XkA/edit?usp=sharing&ouid=110003278384779874308&rtpof=true&sd=true
No email signup. Just make a copy and run the numbers.
RESOURCES & PROGRAMS MENTIONED
Down Payment Resource: https://downpaymentresource.com/
FHA owner-occupied financing: https://www.hud.gov/helping-americans/loans
NACA: https://www.naca.com/
Chicago HomeGrown Purchase Assistance Program: https://www.chicago.gov/city/en/depts/doh/provdrs/homebuyers/svcs/HomeGrown.html
Property examples are presented for educational purposes. Financing, expenses, rents, property condition and individual circumstances vary. Verify property and program information independently before making purchasing or financing decisions.
Property prices and examples featured in this episode are from the Chicago market and are not representative of real estate prices nationwide. Property Sources: public MLS/listing records and sale histories accessed 2025/2026
🎙 Subscribe to Rental Problems Solved for real stories, real lessons, and real solutions from nearly two decades of investing in Chicago real estate.
---
Every rental problem has a solution.
Keep going.