I've invested in Windsor for the past 2 years, and am making some excellent returns. I currently own 3 properties in the Windsor area, 2 triplexes and a single family home. These are the numbers on a triplex that I purchased 2 years ago:
Cost: $255,000
Gross Income: $36,000 + utilities
Net Income: $27,000
Cashflow: $15,500
Cash on Cash Return on $56,000 investment: 27.7% per year
I would definitely recommend multi-family, as your cash on cash return is almost always higher than single family for a variety of reasons (more income, lower vacancy, CCA, etc.). Check Kijiji and MLS. My Realtor down in Windsor gives me the pocket listings before they hit MLS, so that's usually where some good money-makers are to be found.
If you are open at all to looking at some potential deals Windsor, I'd highly recommend it! The market and economy has really started to pick up, with house prices still well below Ontario's average - lots of potential growth for sure. I can connect you with my Realtor and put in a good word for you if you'd like.
Also my investing partners and I are purchasing a larger apartment building this year, something similar in size and CapRate as this one:
https://www.realtor.ca/Commercial/Multi-family/17040993/525-WYANDOTTE-Street-West-WINDSOR-Ontario-N8Y2Z8 If you're interested in learning more, please message me.
Would love to hear from some fellow Windsorites and investors, looking forward to connecting!
P.S. Stay away from Sandwichtown, far away. Walkerville is where it's at!