From Florida Fixer-Uppers to Muskoka Vacation Resort for 70 With Rachel Holden

Hello and welcome to the Truth About Real Estate Investing Show, my name is Erwin Szeto host of this 300+ episode show since 2016.

Thank you to the over 200 folks who attended our virtual tour of US income properties, this was our first time ever and based on the demand and feedback, we’ll be doing this at least once per quarter to satisfy everyone’s curiosity into what direct investing into a US income property looks like. We shared pictures, home inspection reports, renovation quotes, we walked through the numbers which are incredibly detailed including assumptions for vacancy and appreciation rate.

I personally love all the feedback on how investing in landlord friendly USA is totally different than Ontario or BC.  I was on a Zoom with a lady investor from Vancouver who buys condos and the look of surprise and relief when I showed her some properties in top cities for investment like Dallas, Texas or Atlanta, Georgia… she was shocked that opportunities in the $2-300,000 existed that rent for 1800-2400 per month plus utilities that cash flow.

For those who’d like a deeper understanding of how to invest in the USA we are happy to announce our next US investing workshop in Saturday April 13th.  The link to register is in the show notes!

Link to register/details:

From Florida Fixer-Uppers to Muskoka Vacation Resort for 70 With Rachel Holden

In this enlightening episode, Rachel, with a background in advertising managing a $65 million budget and a significant journey in real estate investment from growing up in a duplex to owning investment properties in Florida, investing in duplexes and garden suites in Barrie, Ontario to now full blown cottages resort business owner and operator in Muskoka.  Rachel’s story of strategic investment and personal growth. Our conversation touches on the challenges of property management, the insights gained from renovating and selling properties, and her aspirations to contribute positively to societal health through real estate.

Cottages and short term rentals are a hot topic in the community, Rachel has experience in both short and long term rentals, she’s a no BS kind of gal, she’s obviously smart, you don’t get $65 million dollar advertising budgets to manage for some of the most recognizable brands in the world at two of the top 10 advertising agencies in the world.

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Before you go, if you’re interested in what kind of properties I am looking at in the landlord friendly states of the USA please go to for what I consider the best investment for most Canadians, most of the time.

I’ve been investing in Ontario since 2005 and while it’s been a great, great run. I started out buying properties in the 100,000s and now it’s $800,000 to $1,000,000.  How much higher can it go? I don’t know

To me, the remaining potential for appreciation does not match the risk hence I’m advising my clients to look to where one can find rental properties that are affordable range of $150,000 to $350,000 US$, with rents that range from $1,400 to 2,600/month plus utilities.   As many Canadians recognize, these numbers will be positive cash flow and are night and day compared to anything locally. Plus the landlord has all of the rights, no rent control, and income is US dollars which are better than Canadian dollars.

If you don’t believe me, US dollars are better than Canadian dollars, go ask 100 non-Canadians which currency they prefer to be paid in.

So to regain control of your retirement planning.  Go to and check out what great cash flow properties are available in the USA.  

The best part is, my US investments will be much more passive compared to by local investments as I’m hiring an asset manager called SHARE to hand hold me through the entire process.  As their client and shareholder, Share will source me quality income properties, help me with legal structure and taxes, they manage the property manager and insurance provider while passing down to me preferred rates so I save both time and money.  

Share will even tell me when to strategically refinance or sell.  SHARE can even support investors all over the country for proper diversification hence my plan is to own in Tennessee, Georgia, and Texas.  Share is like my joint venture partner but I only have to pay them fees while I keep 100% ownership and control.

If your goal in investing is to increase cash flow, I don’t know of a better strategy for most Canadians most of the time.  One last time that’s to see what boring, cash flowing real estate investing can look like on your path towards financial peace.

This is how I’m going to make real estate investing great again for my family and hope you choose the same.  Till next time!

Sponsored by:

This episode is brought to you by me! We don’t have sponsors for this show. I only share with you services owned by my wife Cherry and me.  Real estate investing is a staple in my life and allowed me to build wealth and, more importantly, achieve financial peace about the future, knowing our retirement is taken care of and my kids will be able to afford a home when they grow up.  If you, too, are interested in my systematic strategy to implement the #1 investment strategy, the same one pretty much all my guests are doing themselves, then go visit and register for our next event.

Till next time, just do it because I believe in you.



As a committed advocate for transparent and responsible real estate investment, I want to openly share my involvement with SHARE SFR (Single Family Rental) as an Advisor. I hold an equity position in this company and receive a referral commission for clients I introduce to their services. My endorsement of their business model – focusing on direct ownership of positive cash flow income properties – is consistent with my own personal investing since 2005, is based not only on a professional assessment but also on my personal experience and belief in their approach. Please note that while I stand behind my recommendations, it is crucial for each individual to conduct their own due diligence and consider their unique circumstances before making any investment decisions. As always, my priority is to provide you with honest, insightful, and practical real estate investment education.
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