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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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.
By Hudson Smith November 12, 2025
When the snow starts to fall, it has a way of transforming everything — streets, parks, and even front yards take on a quiet, magical charm. But for sellers, winter can also mean extra effort to make sure that charm extends to your home. Curb appeal doesn’t hibernate when the temperature drops — in fact, it matters even more. Here’s how to make your home shine this season and capture that “warm welcome” feeling buyers love, even on the coldest day. Light the Way Winter days are short, which means lighting plays a starring role. Swap out dim porch bulbs for bright, warm-toned LEDs and consider adding soft string lights or lanterns along your walkway. A well-lit entryway not only looks beautiful in twilight photos — it instantly feels inviting. Add a Pop of Colour When the landscape is all whites and greys, a bold front door makes a statement. Deep navy, forest green, or classic red can instantly lift a neutral exterior. If you’re not ready to repaint, a colourful winter wreath or fresh greenery can achieve the same welcoming effect. Dress Up with Winter Greenery Who says planters are only for summer? Evergreen boughs, birch branches, and pinecones arranged in large planters add life and texture to your front entry. They photograph beautifully and bring natural warmth to even the snowiest setting. Keep It Clean and Clear Shovel paths, sprinkle salt, and make sure steps are safe and tidy. It’s one of the simplest ways to show care — and it makes a lasting first impression for both buyers and photographers. Bonus: a clean driveway and entryway make your listing photos feel crisp and polished. Set the Scene for “Cozy” Winter buyers are looking for warmth — literally and emotionally. A soft glow from the windows, a hint of smoke from a chimney, or a front door framed by lanterns all help tell that story. These small touches help buyers imagine themselves stepping into comfort after a snowy day. Thinking of Selling This Winter? A fresh layer of snow doesn’t mean you have to wait until spring. With the right presentation, your home can look more inviting than ever. Selling in winter? We’ll make sure your home stands out — even when everything’s covered in snow. hudson@hudsonsmith.ca | 519-821-3600 | hudson@hudsonsmith.ca
By Hudson Smith October 28, 2025
Halloween in Guelph is more than just costumes and candy — it’s that magical mix of community, creativity, and crisp autumn air that makes this city feel like home. Whether you’re searching for the perfect pumpkin, planning a cozy movie night, or looking for a fun local event, Guelph has something for every kind of ghoul and goblin. Pick the Perfect Pumpkin at Strom’s Farm A Guelph fall tradition! Strom’s Farm & Bakery offers everything from corn mazes and wagon rides to caramel apples and cider doughnuts (trust us — you’ll want seconds). Wander through rows of pumpkins to find your favourite and snap a few festive photos along the way. 📍 5089 Wellington Rd 32, Guelph, ON N1H 6J4 Fall Markets & Family Fun October weekends are filled with local markets and events, from the Aberfoyle Antique Market to smaller pop-ups throughout the city. Browse for vintage décor, locally made candles, and cozy knits — or enjoy a warm drink while supporting local makers. Nothing says “autumn” like spending a Saturday outdoors with something pumpkin-spiced in hand. Get Spooked (in a Fun Way!) at Bingemans Screampark Looking for thrills beyond the city limits? Just a short drive away, Bingemans Screampark in Kitchener delivers haunted houses, eerie mazes, and live actors ready to give you a fright you won’t forget. It’s a must-visit for anyone who loves a good scare — best enjoyed with friends and plenty of bravery. 📍425 Bingemans Centre Drive, Kitchener, ON N2B 3X7 Trick-or-Treat Hotspots Around Town From the charming porches of Exhibition Park to the family-friendly streets of Westminster Woods, Guelph’s neighbourhoods truly shine on Halloween night. Expect glowing jack-o’-lanterns, creative costumes, and friendly neighbours handing out treats. Cozy Up at Home If your perfect Halloween involves staying in, make your home the main attraction. Light a candle, pour a cup of cider, and stream a classic like Hocus Pocus or The Addams Family. Add a touch of “moody modern” décor — think black taper candles, amber glassware, and autumn florals — for a look that’s more sophisticated than spooky. Happy Halloween from the Hudson Smith Real Estate Group! Whether you’re out exploring pumpkin patches, trick-or-treating with the kids, or cozying up at home, we hope your Halloween is filled with laughter, community, and a little bit of magic. If you’re thinking about making a move before the year wraps up, our team is here to help you find a home that’s scary good. hudsonsmith.ca | 519-821-3600 | hudson@hudsonsmith.ca
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