waldo,
Don't know where you get your info from? 
300 folk are selected + some more from sponsors etc.,
About 440 apply - not 2000. 
First timers have a good chance of getting in - if they have some backpacking experience and preferably in Scotland.
Those who do 10 or more crossings (Legends or Leg ends) are in the same draw. They get no special automatic entry.
It is a great multinational event. There is no elitism!
One of the reasons I put my Notes on here was to highlight and commend to others a marvelous backpacking experience.