Here is a nice short answer IMHO
Is it worthy of A League. Yes, about right, easy to solve but plenty to tweak. Just a little time consuming due to its randomness where luck can play a big part as sendai45 has found.
Were the Prices right Yes.
Was it fun Yes.
Was the Contest Duration right Near enough, but most A league contests are only run for 3 to 4 days. Contest duration is not set in stone and you, as the host, can always make it longer or shorter. Looks like this one could end tonight.
Were the Rules clear enough Your rules did state quite clearly that, and I quote -Rules are standard - Prices are modified - Answers are dollarsleft PLUS $500 for each 'dillo in it's correct home)
Natural 'dillo in the top Natural Portal =$500. This can only mean that to get the bonus each Dillo has to go to its corresponding coloured portal (that is its correct home) not that you can put them all in the top blue one (that is only the correct home for the yellow Dillo). So IMHO yes.
Can you play AR2 if you can only see in Monochrome Obviously if severely colour blind it would be a problem when multiple coloured Dillos are involved, maybe Peter could produce an edited version with numbered Dillos.
What do the medals in the Smilies stand for - And do I have to dish one out to the winner There was a time, not so long ago, when we had the Gold medal for Light solutions and the Brown one for Dark solutions and there is a section somewhere on the site that kept a record of who had won what. Now it is just the Gold medal for a win. The Blue medal was used before my time but I think it was used for design awards.