I just purchased an Investment Prop in Orillia (I currently have a small portfolio in Barrie)....I was a bit hesitant at first, but my Realtors encouraged me to take a look (Matthew Johnston & Domenic Gagliardi, they specialize in the Barrie & Orillia market)...I'm glad I did!!! Rents are comparable to Barrie, which is awesome!!!! My two unit home in West Ridge (which is close to the LakeHead University & Costco) brings in $3000 per month ($1600 up & $1400 down)
If you have any further questions please let me know Check out www.BarrieInvesting.com - These guys are the real deal!
As Nathan mentioned above, you want to stay close to the Lakehead University, even though, the prices in that area have jumped over past two years, you still have a good chance for a deal this spring.