My experience was the polar opposite. I've always lived downtown or in the Beach(es), yet have always worked in the 905. Before I had a car, the public transit commute was a nightmare of assorted TTC and Go Bus trips taking sometimes two hours or more to get from my job near the airport to my place at Kingston Rd and Vic Park. Once I bought my first car, my world opened up, road trips, super convenience, rapid arrival, etc. I never looked back. Now I live the downtown Toronto life with 5 bedroom Cabbagetown semi with two cars, and work in Markham. My drive to work is usually less than 40 min, drive home about the same. My cars are both reliable and fully paid off, so all I pay for is insurance and gas. My monthly gas and insurance cost on the two cars is about $200, less than the cost of two metropasses.
Now, I'm also a classic motorcyclist, and once you've done that, you really, really, have the sense of freedom that you may seek. Just yesterday I rode up the DVP/404 and then around Lake Simcoe, back down through the Rouge Valley above the zoo and home again. A really wonderful all day experience, all on $7 worth of gas.