Over the years, I’ve learned that certain types of listings consistently create headaches for buyers. Here are the ones I steer clear of:

Estate Sales

• When a property is inherited, sellers often feel like they’ve won the lottery. That usually means unrealistic expectations, minimal flexibility, and homes that haven’t been updated in decades. You end up paying top dollar for a time capsule

Listings Occupied by Tenants

• In Ontario, tenants have significantly more protection than landlords. Even with proper notice, there’s no guarantee they’ll vacate on time. If they refuse, the deal can get dragged into the Landlord and Tenant Board — a slow, unpredictable process that can derail the entire purchase. Buyers cannot simply “evict upon closing.”

Homes Sold As Is

• These are often Power of Sale properties, but not always. “As is” means the seller won’t negotiate repairs or price adjustments, even if the inspection uncovers major issues. In a market with plenty of options, taking on someone else’s problems rarely makes sense.