I know this post is an older one, but I wanted to comment.
The Oshawa market has proven to be a great place for me to invest. I now own three 2-unit properties, and a 9-plex. As a realtor, I have helped over two dozen investors find cash flow generating properties that are building wealth.
Oshawa, to my knowledge has never been a top 10 Ontario city, however, it has a close proximity to Toronto, is appreciating nicely, has a council that is about to pass legislation allowing for many more properties to be turned into two-unit dwelling, and have housing prices far below that of any other city as close to Toronto.
In 2015, the 407 ETR will extend all the way through north Oshawa. Someone will be able to drive from Oshawa to Yonge St in Toronto in 25 minutes. If you haven't been to north Oshawa lately, the builders have focused on upscale homes, and well thought our subdivisions, with all the amenities. North Oshawa have been dubbed "Poshawa" yet values are a fraction the price of Richmond Hill, Aurora, Brampton or Oakville. What do you think will happen when commuters realize they can fly across the city and get into a 4-bdrm 2500 sq ft home for less than the price of a townhome in Markham?
In addition, Oshawa has scene the growth of the University UOIT campus, a resergence in the downtown core, and construction on the Oshawa Centre - when completed the Oshawa Centre Shopping Mall will be the 2nd largest mall in Ontario behind just the Eaton Centre.
Oshawa will always be identified with its blue collar roots and be thought of as a motor city, however, the fate of the city is by no means dependant on the life or death of the Canadian automotive industry.