I feel for you. Our boy is very tolerant so I don't have any brillant suggestions, but he has endured daily ear washes, cleaners, ointment, antibiotics etc... We just douse the ear with cleaner, massage ear, repeat and treat. Ooh and we do this outside so we can really dump the cleaner in and when they shake it all over the place we don't end up having to wipe down the entire kitchen.
Over time the dogs know just getting out the bottle of cleaner means getting a treat.
CJ's mom, it depends on the dog and what actions they are taking to be stubborn.
My male has allergies, so atleast every other day I have to lean and medicate his ears at this time of year. He use to pull some not nice antics on me like lay on his side and plaster his ear against the tile floor. I got tired of the wrestling match so I just decided that I would put his pinch collar on to control him and when we were done he got the best yummie treats. Now all I have to do is have him sit, he sees the bottles and just gives a big sigh. He know he won't get treats until I am done so the sooner I get done the sooner he gets his treats. No compliance, can't get ears done, then he didn't earn his treat. I don't treat dogs unless they earn them.
I have tried raw steak pieces and even tried his favorite hot dogs but he runs away. I started that if he let me touch his ear he would get a treat but he has not let me get past that. The vet wants $150 to sedate him to clean his ear.