Normally, scars take up to 1 year to mature. I ask patients to wait until after the 1 year post-op mark before having scar revision surgery. Each patient heals differently so I would recommend you following up with your surgeon to make sure your scar is healing appropriately
This is an excellent question and partially depends on how much pressure and what type of gear you are wearing. Part of the problem is that you ears may still be numb and it is difficult for you to assess when there is excessive detrimental pressure on the ear. I would consult your surgeon but...
While you may experience reduction of swelling of the ears in the immediate 4-6 week period after an otoplasty, the ears tend to relax over long term over period of 6-12 months and may stick out a bit more. Sometimes, surgeons will slightly overcorrect the ears for this reason.