Other People’s Property Regrets

A few weeks ago, I asked you to send me your biggest property regret and this week, I wanted to share some of the responses.

What do you think the number one regret was?
Surprise, surprise…

“I wish I had purchased more when I had the chance”

“My biggest regret is not buying more when I was younger”

“I should have bought 25 years ago”

“Buy more!”

and my favourite…

“I regret not having a time machine to go back and buy more property”


Just buying property doesn’t guarantee success. Check out these stories…

———- Forwarded message ———
Date: Wed, Aug 11, 2021 at 3:11 PM
Subject: Re: My Massive Regret
To: Chris Gray <chris.gray@yourempire.com.au>


In 2008 I had some inheritance so I decided to invest, after doing much research and listening to people like XXXXXXXX and XXXXXXXX as well as my own research I bought several investment properties over the space of 4 years. One in Jacana Vic, Springfield Lakes QLD, North Haven SA, Seaford Meadows SA, Rockingham WA, Muswellbrook NSW and Bowen QLD and Toowoomba QLD

12 years later my entire portfolio has grown by 4% some of the properties like Bowen and Muswellbrook at one point declined by as much as 30% and even now are not the same price i bought them for 10 years ago.

So after much headache and over 350K out of pocket to support the portfolio over the ten years I am selling the lot.

How could I have got it so wrong if I had bought just one property in Sydney I would be a millionaire by now.

———- Forwarded message ———
Subject: Re: My Massive Regret
Date: 12 August 2021 at 2:20:41 pm AEST
To: Chris Gray <chris.gray@yourempire.com.au>

Six years ago, I was earning a lot less money so I bought a string of cashflow properties from XXXXXXXX. In that time , there has been very little capital growth (almost none).

Rentvesters until now, we are buying our first home to live in, so as I look for properties to sell to fund the non-deductible debt, I find no equity in those older properties to make that happen.

(As I write all of this, I realise I’m breaking all of those contrarian rules of yours that I really love – but wifey really wants her own place…)

Love your work Chris!


These two emails were from people who actually purchased property years ago… just not in blue chip locations.

Both of them purchased properties in “hot spots”, or on the premise they were “cashflow positive” in regional areas.

Sure, this strategy can work for some people, though it’s just not what I recommend, or is what I did personally.

I’ve always advocated the purchase of property:

  • Blue chip
  • Median priced
  • 5-15 km from the CBD


There will always be a rental demand for properties in blue chip areas. Blue chip properties are more likely to hold and increase in value despite whatever is going on in the economy.

We can’t change the past, but we definitely can create a different future.

If you need help getting started, want to make sure you are on the right path, or want an expert set of eyes to look over your current strategy, it’s not too late.

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