- 15
- Episodes
- Weekly
- Cadence
- 2026
- First episode
About Rental Problems Solved
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
- Publisher
- Robin Williamson
- Category
- business · business · education
- Language
- en
- Explicit
- No
- First episode
- 22 Jul 2026
- Latest episode
- 22 Oct 2026
Latest episodes
15 episodes in the feed.
22 Oct 2026
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
15 Oct 2026
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.
8 Oct 2026
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.
1 Oct 2026
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.
24 Sept 2026
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.
17 Sept 2026
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.
10 Sept 2026
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
3 Sept 2026
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 (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/ (https://downpaymentresource.com/) FHA owner-occupied financing: https://www.hud.gov/helping-americans/loans (https://www.hud.gov/helping-americans/loans) NACA: https://www.naca.com/ (https://www.naca.com/) Chicago HomeGrown Purchase Assistance Program: https://www.chicago.gov/city/en/depts/doh/provdrs/homebuyers/svcs/HomeGrown.html (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.
20 Aug 2026
The Fire Ended. The Hard Part Didn't.
A fire at one of my properties started in a single apartment. We thought it was over. Then the building caught fire again. What followed was nearly a year of recovery — damaged apartments, insurance claims, securing a vacant building, frozen pipes, smoke remediation, contractors, construction delays and hundreds of decisions that had to be made while I was already exhausted. In this episode of Rental Problems Solved, I'm sharing the full story — including the moment I walked through the building alone, looked at the damage and honestly thought: “I don't think I'm gonna be able to do this.” But I didn't really have a choice. I had to figure out what came next. This episode isn't just about what happens during a fire. It's about what happens after the emergency crews leave — and the decisions property owners may face while trying to protect the property, the business and themselves. We’ll get into emergency response, insurance, property security, secondary damage, smoke remediation, rebuilding, managing contractors and the lessons I would carry with me if I ever had to face something like this again. Real stories. Real lessons. Real solutions. Watch the on YouTube @RentalProblemsSolved — Every rental problem has a solution. Keep going.
13 Aug 2026
Would You Catch These Fake Documents Before Renting Your Property?
Everything looked fine... until I started asking questions. Fake pay stubs. Questionable tax documents. Employment that couldn't be verified. In today's world, fraudulent rental applications are becoming more convincing than ever. In this episode, I walk through a real screening process that uncovered multiple warning signs—and share practical ways to protect yourself before approving an applicant. If you're a new or experienced property owner, this episode could save you thousands of dollars and months of headaches. 👇 Download my FREE 10 Investor Action Steps Guide https://legacylivingrobin.mykajabi.com/opt-in (https://legacylivingrobin.mykajabi.com/opt-in) 🎙️ Subscribe to Rental Problems Solved for real stories, real lessons, and real solutions from nearly two decades of investing in Chicago real estate. 🎬 Watch the episodes on YouTube. Because chaos will come... Every rental problem has a solution. Keep going.
6 Aug 2026
What Would You Do If Police Surrounded Your Property Before a Showing?
I thought I was meeting another agent for a routine property showing. Instead... the street was blocked off by police. What happened next reminded me that real estate is about much more than buildings. Sometimes the biggest lesson isn't about negotiating a deal; it's about staying calm when everyone else isn't. In this episode, I share one of the most unexpected experiences I've had as a property owner and the lessons it taught me about people, leadership, and knowing when to trust your instincts. 👇 Download my FREE 10 Investor Action Steps Guide https://legacylivingrobin.mykajabi.com/opt-in (https://legacylivingrobin.mykajabi.com/opt-in) 🎙️ Subscribe to Rental Problems Solved for real stories, real lessons, and real solutions from nearly two decades of investing in Chicago real estate. 🎬 Watch the episodes on YouTube. Because chaos will come... Every rental problem has a solution. Keep going.
30 Jul 2026
The Day an Entire Appliance Truck Disappeared
One move-in. One phone call. And suddenly, an entire appliance delivery truck had disappeared. In this episode of Rental Problems Solved, I share the unbelievable story of a delivery that went completely off the rails, and the lessons every property owner can learn about responsibility, reducing vacancy time, attracting better applicants, and avoiding costly leasing mistakes. Whether you're renting your first property or managing multiple units, small decisions before a tenant moves in can save you weeks of frustration later. 👇 Download my FREE 10 Investor Action Steps Guide https://legacylivingrobin.mykajabi.com/opt-in (https://legacylivingrobin.mykajabi.com/opt-in) 🎙️ Subscribe to Rental Problems Solved for real stories, real lessons, and real solutions from nearly two decades of investing in Chicago real estate. 🎬 Watch the episodes on YouTube. Because chaos will come... Every rental problem has a solution. Keep going.
23 Jul 2026
What Would You Do If the Repairs Weren't the Real Problem?
What happens when you fix everything... and the complaints never stop? In this episode of Rental Problems Solved, I share one of the most frustrating tenant situations I've experienced in nearly two decades as a Chicago real estate investor. What started as routine move-in repairs turned into months of repeated maintenance calls, multiple contractors, a brand-new water heater, an electrician, an eviction case, and one discovery that changed how I looked at the entire situation. Along the way, you'll learn: ✔️ When tenants can and cannot legally withhold rent in Chicago ✔️ Why documentation is your greatest protection ✔️ How to recognize complaint patterns before they become legal problems ✔️ What Illinois law actually says about habitability and repair obligations ✔️ The courtroom lesson every property owner should know This isn't just a story about maintenance. It's about understanding the difference between fixing a repair... and managing risk. 🎙 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.
23 Jul 2026
The Day I Almost Walked Away From Real Estate
A sock. I never imagined something so ordinary could become the moment that changed my life. While selling an apartment building, I found myself dealing with one problem after another: a flooded basement, a tenant's death, bed bugs, financial pressure, and the overwhelming feeling that maybe it was time to walk away from real estate altogether. Instead, that moment became the beginning of something much bigger. In this first episode of Rental Problems Solved, I'm sharing the story that almost ended my investing journey and why it ultimately became the reason this show exists. Whether you're a new investor, an experienced property owner, or simply someone working through difficult seasons, I hope this episode reminds you that your biggest challenges can become your greatest milestones. In this episode: • The unexpected event that nearly ended my real estate career • The emotional cost of investing when everything goes wrong • Why I almost sold every property I owned • How one moment completely changed my perspective • Why your story matters more than you realize This is just the beginning. 🎙 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.
22 Jul 2026
Welcome to Rental Problems Solved | Real Stories. Real Lessons. Real Solutions.
Welcome to Rental Problems Solved. Behind every property is a story. Behind every story is a decision. And every decision leaves a lesson worth sharing. If you're looking for honest conversations about real estate investing not just the highlight reel you've found the right place. From fires and floods to difficult tenants, insurance battles, buying decisions, and unexpected twists, each episode shares a true story and the lessons that came from living it. 🎙️Subscribe and join me as we uncover the stories behind the properties and what every investor can learn from them. 🌐 Learn more and find additional resources at LegacyLivingRobin.com
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