To be honest it's nearly impossible to race with a keyboard when driving non-demo cars anyway. Even the demo cars on Fern Bay or South City are harder to control then on Blackwood. Especially with other racers around you.
At least a mouse or an analog gamepad should be used. Really!
It's a different world out there
About winning... In theory anyone could win. Faster drivers are winning more easily but the one who drives more often also has a good chance. Some high ranked racers don't have a very fast Personal Best. Sometimes you can gain on a faster driver because he/she fails somewhere... The pit requirement also plays an important role.