Rental Problems Solved

Robin Williamson
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  • Investing
  • Weekly

Rental Problems Solved is a real-world real estate show sharing real stories, real lessons, and real solutions through the experiences that shape investors. Behind every property is a story. Behind every story is a decision. And every decision leaves a lesson worth sharing. From fires, floods, insurance battles, difficult tenants, renovation surprises, market shifts, and unexpected moments that change everything. Each episode follows a true story and the lessons that came from living it. If you're tired of highlight reels and surface-level advice, you're in the right place. Whether you're buying your first property, growing a portfolio, or simply curious about what ownership really looks like, these stories offer an honest look at the challenges, decisions, and resilience behind real estate investing. New episodes released weekly, every Thursday. Subscribe and follow along as we uncover the stories behind the properties and what every investor can learn from them. 🌐 Watch full episodes, listen to the podcast, and explore more at: LegacyLivingRobin.com

  1. Oct 22

    Chicago’s New Rental Proposals: PRO vs. FAIR — What Would Actually Change?

    Chicago is considering two competing proposals that could change the rules for renters and housing providers: the Protecting Renters Ordinance (PRO) and the Fair and Accountable Illinois Rental Ordinance (FAIR).   But what would actually change, and what’s already part of Chicago’s Residential Landlord and Tenant Ordinance (RLTO)?   I went through the proposals after realizing that some of the provisions I thought were new already exist under Chicago law. In this episode, I compare the current RLTO with PRO and FAIR, including repair-and-deduct rules, rent withholding, rental registration, security deposits, application and move-in fees, and the proposed rental-housing offices.   I also share one of my own rental problems: a lease-violation case involving serious sanitation conditions that took nearly nine months to resolve. That experience left me with a different question: when a housing provider has a legitimate problem with a resident, what practical help is available before the problem ends up in court?   PRO and FAIR are both proposals as of this recording and can still change. Current source documents and additional reporting are linked below.   Every rental problem has a solution.   Keep going.   Chapters 00:00 Who Helps the Housing Provider? 1:44 Why I Started Reading Chicago’s PRO Ordinance 2:55 What Chicago Renters Can Already Do Under the RLTO 4:26 PRO vs. FAIR: What Would Actually Change? 6:29 The Rental Problem That Took Me 9 Months to Solve 8:41 Could Chicago’s New Rental Offices Help? 9:35 Rental Registry, Fees & Privacy Questions 10:56 What Eviction Data Doesn’t Tell You

  2. Oct 15

    These Celebrities Were Evicted Before They Were Famous — What Happened Next?

    Long before the success, fame and careers we know today, the celebrities in this episode faced something millions of people can relate to: housing instability, including eviction.   In this episode of Rental Problems Solved, we look at what happened before the success, then turn to the question that matters if you’re facing financial trouble now: What should you do if you can’t pay your rent or mortgage?   We’ll talk about communication and payment arrangements, finding current rental and legal-aid resources, mortgage repayment plans, forbearance, loan modifications, credit reporting, foreclosure timelines, and why investment-property loans can require a different strategy — including the possibility of default interest.   Programs, eligibility and laws change by location and over time. Use the resources in this description as a starting point and confirm what applies to your situation.   Every rental problem has a solution.   Keep going. -- Disclaimer: This content is for educational and informational purposes only and should not be considered legal, financial, tax, or professional advice. Laws, programs, and individual circumstances vary. Always consult a qualified professional regarding your specific situation.

  3. Oct 8

    Is Real Estate Investing Still Worth It?

    After almost two decades of investing in real estate, I've dealt with fires, theft, repairs, insurance problems, financing challenges, contractors, tenant issues, and plenty of moments when I've wondered whether all of this is actually worth it.   So in this episode, we're talking about the other side.   What can real estate actually add to your life? What does it require from you in return? And if you're considering becoming a full-time investor, what should you think about before leaving traditional employment?   We'll look at today's housing market, the lifestyle benefits people don't always talk about, the problems that come with owning property, and some things I wish I'd understood before becoming self-employed full-time.   I'm not here to tell you whether you should invest. After seeing both sides of this business, I can tell you why real estate is still worth it for me, and give you more information to decide what makes sense for you.   Every rental problem has a solution.   Keep going.

  4. Oct 1

    Can You Evict a Tenant for Hoarding?

    I thought I knew the solution when I discovered severe accumulation and sanitation concerns inside an apartment: lease violation, call the attorney, start the eviction process.   Then I learned the situation could be much more complicated.   In this episode, I share what happened in my building and then look at the harder question I did not have to fully test at the time: what if the resident had been paying rent on time?   We look at Illinois fair-housing guidance, several court cases with different outcomes, and the practical systems I would use now; routine inspections, vendor escalation standards, objective documentation and a measurable compliance process.   This episode is educational and is not legal advice. Housing and fair-housing rules vary by jurisdiction and facts; consult qualified local counsel for an actual case.   🎙 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.

  5. Sep 24

    The Water Wouldn't Stop...Then the Plumber Disappeared

    What would you do if water was pouring through multiple apartments, and neither the building shutoff nor the city shutoff would stop it?   What started as a small puddle became nearly 3 days of water, city crews, the fire department, unavailable plumbers, a contractor problem, new holes in copper pipes, demolition and drying.   Then we finally found the original cause: one tiny nail.   In this episode of Rental Problems Solved, I walk through what happened and the emergency systems I would put in place before the next leak ever starts.   🎙 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.

  6. Sep 17

    Why Is Property Insurance Getting So Expensive?

    What happens when property insurance stops feeling like a normal operating expense and starts changing whether the investment still works?   After seeing premiums climb and then receiving a quote of roughly $40,000, I started digging into what is happening in the insurance market, not only in Chicago, but across the country.   In this episode, I look at why multifamily property insurance costs have risen, why some regions are being hit harder than others, how homeowners are being affected, and what property owners can do when the brokers and carriers they already know seem to have run out of options.   This episode is based on my own experience plus public research and is for educational purposes only. Insurance availability, underwriting and coverage vary by property and market.   🎙 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.

  7. Sep 10

    The Deadliest Porch Collapse in U.S. History: What Went Wrong?

    In 2003, a late-night party in Chicago ended when two levels of rear wooden porches collapsed, killing 13 people and injuring dozens more. I remember hearing about it and wondering two things: Why were so many people on the porch, and how would anyone know how many people a porch could safely hold?   More than twenty years later, I went back to find out what happened after the headlines disappeared. In this episode of Rental Problems Solved, we look at the party, the questions surrounding the porch itself, earlier City inspections, years of lawsuits and insurance disputes, and the practical lesson for anyone who owns a rental property, or simply has an elevated porch, balcony or deck at home.   This episode is based on court records, City of Chicago records and reporting from the time. Some historical sources differ on the exact number of people on each porch level, so those differences are noted rather than treated as settled fact.   🎙 Subscribe to Rental Problems Solved for real stories, real lessons, and real solutions from nearly two decades of investing in Chicago real estate.   Because chaos will come... The key is learning how to profit through it. Every rental problem has a solution. Keep going.   SOURCES FOR THIS EPISODE • Illinois Appellate Court — Ware v. City of Chicago (2007) • Illinois Appellate Court — Ware v. First Specialty Insurance Corp. (2013) • CBS Chicago — 20 Years After the Lincoln Park Porch Collapse (2023) • CBS/AP — Deadly Porch Had No Permit (2003) • City of Chicago Data Portal — Building Violations / Inspection Categories • City of Chicago — Building Permit and Inspection Records / 311 inspection resources

  8. Sep 3

    Think 2008 Type Real Estate Deals Are Gone? I'll Show You They're Not in 12 Minutes

    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.

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Rental Problems Solved is a real-world real estate show sharing real stories, real lessons, and real solutions through the experiences that shape investors. Behind every property is a story. Behind every story is a decision. And every decision leaves a lesson worth sharing. From fires, floods, insurance battles, difficult tenants, renovation surprises, market shifts, and unexpected moments that change everything. Each episode follows a true story and the lessons that came from living it. If you're tired of highlight reels and surface-level advice, you're in the right place. Whether you're buying your first property, growing a portfolio, or simply curious about what ownership really looks like, these stories offer an honest look at the challenges, decisions, and resilience behind real estate investing. New episodes released weekly, every Thursday. Subscribe and follow along as we uncover the stories behind the properties and what every investor can learn from them. 🌐 Watch full episodes, listen to the podcast, and explore more at: LegacyLivingRobin.com

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