You can watch the YouTube video here.

With cooling market conditions, tax changes and another rate rise expected this year, uncomfortable decisions are starting to surface for many investors.  

In this jam-packed Q&A Day, Ben is joined by Couch Crew, Ben Thompson (QPIA) and Shane Pope (Buyers Agent), to tackle four real scenarios facing property investors right now. 

  • Should you sell a good property when cash flow gets tight?  
  • Have recent tax changes fundamentally changed the investment equation?  
  • What happens when the regional portfolio you built to eventually buy your dream home starts falling behind? 
  •  And can you realistically wipe out your home loan in five years?

Plus, Ben opens the episode with an important warning about the hype, false scarcity and short-term promises appearing in parts of the buyer’s agent industry , and why changing market conditions could expose investors who bought speculation rather than quality. 

From cash buffers and debt reduction to fear of messing up, portfolio exits and knowing when to seek professional advice, this episode is about making the invisible visible before making your next big financial move. Listen now!  

 

Free Stuff Mentioned

🎟️ Sell, Hold or Optimise Webinar
7:30pm AEST, Tues 22 September
Register for our upcoming webinar on how to make the right property decision in the current market, including whether to sell, buy or sit tight.
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🎥 Updated Case Study Series
See how the original strategies from How to Retire on $3,000 a Week stack up under today’s tax settings, plus a brand-new bonus Live-Vesting case study. Usually $197, Couch Crew can access the full series for just $17 using code COUCH17.
👉 Save $180 on your updated Case Studies

🎤 Guests & Episodes Mentioned:  

  • 564 | From FOMO to COMO: What Compromise Gets You Into the Property Market? 
  • 610 | Livevesting: Could Buying a Better Home Be Smarter Than Another Investment Property? – Chat with Stuart Wemyss 

🏠 Download the Rental Property Owner’s Playbook and get a practical system for staying on top of your investment property — from the day you buy through to tax time, ongoing reviews and eventually selling.

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Timestamps

  • 00:00 — 614 | Property D-Day: The Decisions Investors Can’t Avoid – Q&A Day  
  • 00:36 — Buyer’s Agent Hype: Ben Gets on His Soapbox for a Critical Warning  
  • 08:05 — Housekeeping: Sell, Hold or Optimise + Couch Crew Offers  
  • 11:45 — Q1: Should We Sell a Good Property When Cash Flow Gets Tight?  
  • 21:28 — Q2: What If Everything Goes Wrong?  
  • 34:29 — Q3: Is Our Dream Home Getting Further Away?  
  • 46:06 — Q4: Can We Pay Off Our Home Loan in Five Years?  
  • 52:51 — Send Us Your Question, Have It Featured + Get the Case Studies FREE 

 

Questions We Answer

Q1: Should We Sell a Good Property When Cash Flow Gets Tight? from Sam  

“Hi legends, we’re a couple in our late 30s earning around $150,000 and $120,000 respectively. We currently own three properties. Our newly built home is worth around $2.3 million with $800,000 owing. We also have an investment property in Toowoomba worth around $900,000 with $630,000 owing, and another in Geelong worth around $880,000, with a similar amount owing. 

We believe they’re all good assets, but with my wife on maternity leave this year and next, the holding costs are starting to put some pressure on us. Given the current market and our level of exposure, is now the time to consider selling the Toowoomba property?” 

Q2: What If Everything Goes Wrong? From Cassandra  

“I’m single with no kids and have built up some equity in my principal place of residence. I’ve been considering using that equity to invest, but with the recent tax changes, I’m starting to question whether my original plan still makes sense. 

I’m also worried about what could happen if my home falls in value or I lose my job. My mind tends to jump straight to the worst-case scenario — not being able to keep up with the repayments and potentially having to sell my home. 

How can I work through these fears and get some confidence back in my plan? My friends keep telling me to stay away from property altogether and invest in blue-chip shares instead.” 

Q3: Is Our Dream Home Getting Further Away? From Jack 

“We’re a young couple with three investment properties worth around $1.9 million combined. We’ve held them for three to four years in regional areas that have experienced decent growth. Our end goal is to buy a home in Sydney worth around $1.9–$2 million. 

Our concern is that Sydney property may be growing faster than our investment portfolio — meaning the longer we hold, the further away the home we actually want could become. How should we think about that growth differential, and whether our current portfolio is still helping us reach that end goal?” 

Q4: Can We Pay Off Our Home Loan in Five Years? From Mike  

“Hi Ben, thanks for all the insights. 

We currently have two investment properties in Keperra and Frankston, plus a $555,000 loan on our principal place of residence, with $150,000 sitting in the offset. We also have around $45,000 in shares and $200,000 in combined super. 

In five years, one of us is hoping to reduce our working hours. Ideally, by then we’d like to have paid off our home while still holding both investment properties. What should we be prioritising over the next five years to put ourselves in the best position to achieve that? And realistically, is paying off the PPOR within that timeframe achievable?”