A couple of questions concerning this:
No, leaving out that semicolon will introduce a great amount of risk in your application, it will be all too easy to overlook adding it back if you add more styles to your element. At that point, you are relying on your manual processes and attention to detail to ensure you didn't accidentially misplace on of your non-semicolon lines. Worse yet, you would have to physically check your css file every time you were ready to go to production to make sure you didn't screw up any of the final style lines in each element.
Possibly, since the file would be smaller, but the difference should be negligible. If you are worried about load times, Gzipping your files before placing them on the server will serve you well.
Most browsers are smart enough to know what you mean, but you still have to worry about screwing up your CSS file by not being careful about the last style.