11 Things I've Learned About Investing In Real Estate

Eleven things I've learned about investing in real estate

I can remember my first experience with real estate investing – walking through the first house I ever bought: a townhouse in the north end.
$86,000 seemed like an awful lot of money back then, but the fact that my dad was so excited about real estate investing reassured me that, at 19 years old, this was the best thing I could do with the $10,000 I had saved.
I originally had a car in mind, but a house was the first thing my dad invested in when he had the money. Looking back, that purchase was motivated more by making him proud than how I would have imagined it was going to positively change my life. The purchase happened quickly. At first, I didn’t understand the investment part but was mostly excited about owning something.

Twenty-four years of real estate investing and a portfolio shaped by that first purchase, I’ve sure learned a lot.
Now I’ve managed to get to a position where I treat every day managing them like a separate job and less of a hobby. After years of talking to others about owning real estate and the investment side of it I have refined my view on it and love to share what I have learned. I am far from the only investor in town and learn something new all the time. I welcome anyone to share their views.

Below is some counsel borne from a couple decades of real estate investing – the good, bad (not much), and ugly (mostly toilet fixing) experiences, and I hope you enjoy the read.
 

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January 13, 2026
There’s nothing quite like realizing you have an extra day off coming up. Statutory holidays (often called stat holidays) are paid days off that give employees in Ontario a chance to rest, recharge, or enjoy a long weekend. Knowing when these holidays fall can make planning your work schedule and personal time much easier. This guide is designed to help you quickly check Ontario stat holidays for 2026, plan time off in advance, and stay organized throughout the year whether you’re booking a vacation, managing schedules, or simply looking ahead to your next break. Below are the official Ontario stat holiday dates for 2026 that you can mark on your calendar. 👉 Download the Free 2026 Stat Holiday Guide
By Hudson Smith December 3, 2025
There’s something special about Guelph in December. The lights feel a little brighter, the downtown feels a little cozier, and the whole city comes alive with traditions that bring our community together. To help you make the most of the season, we’ve put together a simple guide to some of our favourite local holiday events — the ones that make living in Guelph feel like home. Spirit of the Season December 5–7 & December 12–14 — Downtown Guelph Downtown transforms into a festive hub filled with twinkling lights, artisan vendors, live entertainment, and warm holiday energy. It’s the perfect place to support local businesses, enjoy a hot drink, and soak in the magic with friends or family. If you’re looking for that “start of the holidays” feeling, this is it. Sparkles in the Park December 13–31 — Riverside Park Every evening, Riverside Park lights up with spectacular displays — glowing tunnels, festive scenes, and whimsical designs that bring out everyone’s inner child. And this year, keep an eye out for The Hudson Smith Group lighting display among the magic — we’re proud to support this beautiful community tradition with the Guelph Rotary Club. Even better? The carousel rides are free, and there’s a fireworks show on New Year’s Eve. Santa Run & Santa Claus Parade Saturday, December 6 - Santa Run 4:55 PM & Parade 5:30 PM One of Guelph’s most beloved traditions. The evening starts with the Santa Run — a quick, fun, festive dash — followed by the parade winding through downtown with music, lights, and holiday cheer. It’s a great way to kick off December with the whole family. Old Quebec Street Christmas Market Dates vary through December A cozy, European-style indoor market right in the heart of the city. Expect local makers, handmade gifts, warm drinks, and the perfect place to finish (or start!) your holiday shopping while supporting local vendors. Market Square Skating All winter long — weather permitting Nothing feels more festive than skating under the lights in front of City Hall. Bring a friend, grab a hot chocolate afterward, and enjoy one of Guelph’s simplest — and most nostalgic — winter traditions. Giving Back This Season If you’re looking to make a difference this year, consider supporting one of Guelph’s incredible community organizations, including: The Guelph Food Bank Royal City Mission Hope House Toys for Tots / local toy drives Rotary initiatives A little kindness goes a long way during the holidays. From Our Team to Yours The holidays are a time to slow down, reflect, and appreciate the people who make our community special. Whether we’ve worked together this year or you’ve simply followed along with our journey — thank you. Your trust and support mean the world. Wishing you a warm, joyful, magical holiday season from all of us at the Hudson Smith Group.
November 14, 2025
Have you ever wished you could have more space — without sacrificing connection? Across Guelph, more families are embracing two-family or multi-generational living as the perfect blend of connection, independence, and financial practicality. Whether supporting aging parents, welcoming adult children home, or creating separate living quarters for long-term stability, buyers want homes that can comfortably and naturally support two households. But as demand grows, suitable properties have become almost impossible to find—especially in walkable, highly established neighbourhoods like Old University. That’s what makes 36 Harcourt Drive such an extraordinary opportunity: a true two-family home that offers space, flexibility, privacy, and location without compromise.
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