My boy (one of, I have two brothers) has ears problems caused by allergy...called atopy. Our vet thinks its probably dietary but as we take him for runs in the new forest, where nourishment of various sources abounds, a true exclusion diet is just about impossible. We have been using oral steroid, (prednidale) but the side effects made him so miserable that we are now using atopical cortisone spray called cortavance. My boy is quite blase about ear care now provided it is me who does it but if you are having problems, two things that have worked for me are as follows. they are both a bit messy and more wasteful of product than dripping in but they might work if dripping in doesn't.
If the drops are thin, measure them into a very small cap (eg off a small bottle but washed well) and tip the drops into the ear, i don't know why this works but it seems too. For the thicker drops I put on a disposable glove and dispense the drops onto my finger then rub the finger around the ear. You need short short nails if you do this as even through a glove, a long nail can catch a sore ear.