Is an omelette any better when you roll the egg many times over?

It changes the texture.  Better is subject.  If texture is an important feature of food to you you may prefer it or you may hate it.

Makes no difference how many times you roll it over. People that advise differently have no clue what hey speak of. 

You just have to fold it over twice.  This preserves the fluffiness of the omelet, making it lighter.  And it also keeps the omelet fillings tucked inside .. especially important if you are adding grated cheese to your omelet.  Ideally you want a BIT of a "crust" on the outside, with a thick soft spongy layer, and then an inner moist layer with the filling and cheeses combining.

It's easy enough to do. You don't need a special pan.  Just flip the outer 1/3 over onto the center, and then as you slide it out of the pan, slide it so tht you do one more fold-over onto the plate.