Most people think the second investment property is the hardest to buy. But after talking with someone who’s helped clients retire early through real estate, I learned the truth is different.
The first property is actually the toughest. And once you understand why, you can push past the mental barriers holding you back.
Why First-Time Investors Struggle Most
If you’ve been an employee your whole life, taking calculated risks with money feels terrifying. Your brain fights you every step of the way.
The mental side is the biggest battle. You’re learning to trust yourself with big decisions. You’re worried about every little thing that could go wrong. Even when you find a good property, you can’t move fast enough because you’re still asking questions and fighting fear.
But here’s the good news: once you complete that first purchase, get settled in, and see that your fears didn’t come true, building your portfolio gets much easier.
Book Your Strategy CallWhen You’ll Get Your First Real Deal
New investors always want to know when they’ll get their first “steal” – that property that’s way underpriced and builds wealth fast.
The answer? Usually on your third or fourth property.
Why not the first? Three reasons:
- You don’t know what a good deal looks like yet
- Even if you spot one, you can’t move fast enough
- Experienced investors will beat you to it every time
Veteran investors can write an offer in minutes, conditional for just one day to confirm financing. They know their numbers cold. They’re ready to go.
By your third property, you’re ready too. You know what to look for. You understand the numbers. You’ve got relationships with your mortgage specialist and agent. You can move quickly and confidently.
The Smart Way To Start: Skip The Duplex
Many first-time investors buy a duplex with 5% down, living in one unit while renting the other. It sounds perfect.
But here’s the problem: after property two or three, those 5% down programs disappear. You need to bring more money to each deal. Your momentum stalls.
There’s a better way: buy a single-family house where you can add a basement suite.
Four Ways To Add A Second Unit
Here are your options, ranked from cheapest to most expensive:
- Basement suite with side or back exit (cheapest)
- Addition on the back of the house
- Convert a detached garage
- Build a detached unit in the backyard (most expensive)
Most people want to talk about the fancy backyard unit. But the basement suite gives you the best return on your investment.
The BRRRR Method Explained Simply
This strategy lets you recycle your money and build wealth faster:
Buy a house suitable for a basement suite
Renovate it to add the second unit
Rent both units (you can get over $1,000/month in cash flow)
Refinance based on the new higher value
Repeat with the money you pull out
The renovation forces the property value up. When you refinance, you can pull most or all of your money back out. Then you use that money for your next property.
How Mortgage Plus Improvements Works
You don’t need all the renovation cash upfront. Your lender can provide money for both the purchase and the improvements in one package.
This means you’re not draining your bank account. You force the value up through the renovation. You can refinance faster. And you have money ready for the next deal.
Why Most Condos Don’t Work
Out of 179 condos listed for sale in one market, only three made sense as investments.
That’s the reality most agents won’t tell you.
Many condo buildings have serious problems:
- Poor management
- Low reserve funds
- Big repair bills coming
- They don’t cash flow properly
The honest approach? Tell clients which specific buildings work and why most don’t. If you’re a doctor or accountant who needs to sleep at night, you need steady, predictable investments – not problem properties.
New Government Rules Creating Opportunities
Things are changing fast, and smart investors are paying attention.
Faster Approval Process
Getting projects approved used to take two years. Now it takes one year – a 50% improvement.
The new cloud-based permitting system means you submit documents once, not five or six times. You can see exactly who’s holding up your file. And 80% of the time, bottlenecks get fixed within 24 hours.
Pre-Approved Six-Plex Designs
This is huge: federal pre-approved six-plex designs that local bureaucrats can’t stop.
The benefits:
- Only 5% down required (95% financing available)
- If the property is zoned correctly, local officials can’t block you
- Federal approval overrides local objections
Three and Four-Plex Zoning Changes
You can now build triplexes in areas that traditionally only allowed single-family homes. This opens up neighborhoods that were off-limits before.
Fourplexes are likely coming next. British Columbia already allows them by right, and Ontario typically follows BC’s lead within about eight months.
Why Experience Matters
You want to work with people who actually invest themselves. Not just people who sell to investors.
Here’s why: if they use the same property managers, contractors, and mortgage specialists they recommend to you, their advice is tested. They know what works because they do it themselves.
And there’s a powerful alignment: the more successful you become and the more properties you buy, the more they can invest too. Your success drives their success.
Why would they sell you a bad property? As soon as they do, you’re stuck. You can’t buy more. The relationship is over. They want you wealthy and buying bigger and better properties, not stuck with a problem building.
The Adult Treatment
Real professionals treat you like an adult. They give you the good, the bad, and the ugly. They let you make informed decisions.
That’s different from agents who tell you what you want to hear or push properties that serve their short-term commission goals instead of your long-term wealth.
The Inherited Problem Property
The only time serious tenant problems pop up – like tenants not paying rent for six months – is when someone inherits a client from another agent who sold them a bad property.
Solving these inherited problems builds client loyalty for life. It’s like pulling a thorn out of a tiger’s paw. If you fix the problem, they never forget it.
Why Windsor Works For Investors
Windsor-Essex offers something special for real estate investors:
- It’s a major city in Ontario with solid infrastructure
- Much more affordable than Toronto
- Properties can cash flow $1,000+ per month
- Government support for development
- Improving processes for approvals
Toronto investors often understand the opportunity faster than locals, who sometimes take their own market for granted.
The Bottom Line
Your first property is the hardest because you’re fighting your own mind. You’re learning to take calculated risks. You’re building knowledge and confidence.
But once you push through that first purchase, everything gets easier. By your third or fourth property, you’ll be moving fast and spotting good deals.
Start smart with a basement suite instead of a duplex. Use mortgage plus improvements financing to save your capital. Work with people who invest themselves and will tell you the truth.
The path to building wealth through real estate isn’t complicated. But it does require taking that scary first step.
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