Owning property in Windsor, Living in Toronto

[Keith Smith]

Hi,

I'm living in Toronto and considering my first purchase and am looking to hold properties longer term.

I'm attracted to Windsor due to the finances.  I wondering about people's opinions and experience owning a property at a 4hr distance like that. 

Does this imply the need for a property manager? If so, what kind of cost does that incur? If not, how do you typically work around tenant issues, keep an eye on the property etc. 

I was also considering Oshawa due to it's proximity and affordability but haven't yet researched the market.  If not Windsor, what other Cities would you recommend (or not as the case may be).

All insights appreciated.