The 7 Best and Worst Things to Do as a New Real Estate Investor

Diving into real estate investing in Windsor-Essex or Chatham-Kent can be rewarding—but knowing the right steps makes all the difference. Whether you’re eyeing a duplex in Windsor or a rental property in Chatham, here are the seven best and worst moves to guide your investment journey.

✅ The 7 Best Things to Do

1. Educate Yourself: Study local market trends through resources like Stake Realty’s monthly Windsor-Essex market updates or the Chatham-Kent Association of Realtors’ reports. Understanding neighbourhood hotspots like Walkerville or Wallaceburg can help pinpoint opportunities.
2. Work With a Trusted Realtor®: Local experts, such as those at Stake Realty, offer deep insights and connections to off-market deals. “Working with a Stake Realty agent helped me find a multi-unit property in downtown Windsor that fits my goals perfectly,” shares investor Emily R.
3. Focus on Cash Flow: Look for properties that generate positive cash flow. For example, a duplex in Leamington has proven to provide steady rental income even during market dips.
4. Start Small: Many successful investors in Chatham-Kent began with single-family homes before scaling. “My first rental in Chatham was a small 3-bedroom house. It was manageable and gave me confidence to expand,” says local investor James T.
5. Budget for Repairs and Vacancies: Older homes in historic Windsor neighbourhoods like Riverside may need more upkeep. Setting aside a repair fund saved investor Mark S. from surprises when renovating a century-old property.
6. Build a Reliable Team: From contractors to property managers, having trusted local professionals is key. Stake Realty connects investors with vetted service providers to keep investments running smoothly.
7. Know Your Exit Strategy: Plan ahead whether you aim to hold long-term, flip, or refinance. Windsor investor Sarah L. explains, “I always factor in a 5-year hold with potential refinancing to fund my next project.”

❌ The 7 Worst Things to Do

1. Rushing Without Research: Avoid jumping into the first deal. A Windsor investor lost out after skipping a proper market analysis and bought at a peak price.
2. Ignoring Local Market Trends: Not all neighbourhoods appreciate equally—overlooking data from sources like CKAR in Chatham-Kent can lead to poor buys.
3. Overleveraging: Taking on too much debt is risky, especially in fluctuating markets. A local investor’s overextended financing caused stress during vacancy periods.
4. Underestimating Expenses: Property taxes, insurance, and unexpected maintenance in Chatham-Kent can add up quickly, so always factor these into your budget.
5. Skipping Inspections: A Windsor investor who waived inspection on a fixer-upper faced costly repairs later, eroding profits.
6. Neglecting Tenant Screening: Poor tenant choices have led to missed rents and damages in local rentals, emphasizing the need for thorough screening.
7. Going It Alone: Trying to handle everything solo often results in burnout. Partnering with Stake Realty and local experts can ease the burden and boost success.

Final Thoughts

Real estate investing in Windsor-Essex and Chatham-Kent offers many opportunities—but only for those who prepare wisely. Learning from local investors’ successes and mistakes can fast-track your path to profitable investments.

Want to explore local opportunities with expert guidance? Contact Stake Realty today and let’s build your investment portfolio with confidence.