Duke is such a handsome boy, what an adorable face! Sorry to hear his ear is hurting. I think my Mandy was born with an ear infection in her right ear! Everytime it seemed better, next day it was back. She was even taking oral antibiotics and antibiotics that went in her ear. I felt so bad for her! After the last one, months ago, my vet told me to try mixing 1/2 rubbing alcohol and 1/2 white vinegar and using a baby wipe which of course you wring out. She said not to use it while she had the infection. And thank goodness no more ear infections*knocks on wood* I wouldn't tell anyone to try it without their vets advice, of course.
I hope Duke is feeling better soon.