I’ve been investing in real estate for nearly two decades now. My focus? Long-term rentals—both single-family and multi-family units. I’ve also done due diligence on hundreds of vacation rentals, and am working on putting a few properties on the market, though that is a topic for another day.
Now, when I say I’m thorough, I mean it. When I’m in the market for a new property, I typically tour 30 to 50 properties before making an offer. Yep, I’m that investor. I call it my calibration process - seeing enough properties that when the right one comes along at the right price, I know it immediately.
Over the years, I’ve walked away from many properties that didn’t sit right with me, or where the seller’s price expectations were too high. I’ve also abandoned full searches after digging into an area’s economics and realizing it didn’t meet my investment criteria. And I’ve only lost out on one property where I put in an offer —and it was not because of price. That one it still stings, not gonna lie.
Now, let me take you back to that very first property purchase…
It was in 2006, just before the Great Recession.
I had looked at 50 places across the Greater Boston Area. Yep, 50. I went through five realtors in the process, until I found the right one. And I learned something important early on: know your must-haves vs. nice-to-haves. And test them through your calibration process.
I initially thought I needed a parking spot in the city. But after seeing so many properties, I realized that for me and for my budget, it came down to location and layout. I prioritized proximity to work and having two bedrooms. Parking? Garage? Those were nice, but not essential.
In the end, I bought a 900-square-foot, newly renovated condo with two beds, two baths, and low condo fees. It backed up to a park, was a 7-minute walk to the subway, close to the Charles River, and even near a couple grocery stores. Honestly, it was the perfect spot.
It cost me just over $300,000—and I was making about $30,000 a year at the time. So yeah… it felt like a fortune.
I was house poor right away. I had only a few thousand to put toward a down payment. So I had a first mortgage. I had a second mortgage. Condo fees. Utilities. I had to buy furniture and window treatments. It added up fast. I had not planned well enough.
I found a roommate to help cover expenses. And around 2008, 2009 - during the Great Recession, I honestly thought I’d made the dumbest decision ever.
But… here’s the thing. I bought in a good location. I stayed patient. And it paid off.
I eventually paid off my second mortgage and refinanced my primary mortgage to get a lower monthly payment. That cut my costs significantly. And even during the recession, my condo never lost value.
By 2012, prices in my neighborhood started rising.
- I was now living for less than $2,000/month in my 2 bedroom condo
- Equivalent rents were going for $3,000
- I was saving about $1,000/month vs. renting and was eligible for a mortgage tax deduction, which equated to another $500/month … so $1,500 per month of savings vs. renting
- That savings equated to $18,000 in increased cash flow annually in my last few years in that property
In 2015, I listed my condo for just under $500,000 and sold it in less than a week for more than $50,000 above asking—and I netted over $300,000 from the sale after paying off my mortgage and realtor fees.
LET. THAT. SINK. IN.
The property appreciated to 1.8x its original value in 9 years. That is a 7-8% increase in value per year. But here’s the kicker: I put in a total of $85,000 over the 9 years I owned my condo, between my initial downpayment, paying off the second mortgage, and paying for some additional improvements to maximize value prior to sale.
Over 9 years, that $85,000 investment turned into $300,000.
That’s a 3.5x return—equivalent to more than 15% annual growth on my investment.
This kind of return? You won’t find it in public markets. And this, my friends, is why leverage—using loans to invest—is such a powerful tool for building wealth.
With the money saved, I rolled it into a $900,000 two-family property with 25% down. And that’s how it all started.
So that’s my first real estate investment story. The good, the bad, and the lessons I wish I knew.
If you’re just starting out or you’re gearing up for your next property purchase, remember: be patient, be thorough, and always invest in the fundamentals—location, long-term value, and smart leverage. And we’ll dig deeper into each of these topics in future installments.
Catch you next time!
