I think you just need to be a little more firm with her.. I understand that you dont want to hurt your pet, or you dont want to stress them out, but you HAVE to do it.. Getting to the point where it is hardened and coming out of the ear canal, means that it already got a LOT worse.
I suggest getting a second person to help you. One to hold him and comfort him, and one to get in that ear and clean it! I would probably start with a warm wet towel (dont use paper towels, they are scratchy)
Get out as MUCH as you can with the towel. After everything is done, get out you pets favorite treat. I usually don't suggest bacon as a treat unless you REALLY need your dog to forget about what you just did. Bacon is a GREAT treat for this type is situation. If bacon is not do-able, then some boiled chicken, or something like that. It will have to be something very special that they do not get often, this way EVERY time you clean their ears, they will associate the discomfort with getting a super awesome treat at the end.
Then, I would say tackle the inside of the ear the next day, or at least a new hours later. I suggest that you purchase Vet Solutions Brand Ear Cleaner. My vet uses it (as do many) and it is available to the general public. It is great because it has a drying agent in it that is NOT isopropal alcohol. Look on the cleaner you are using now, and see if it has isopropal alcohol in it. If it does, toss it out. That is the reason your dog hates getting his ears cleaned so much. That stuff BURNS! The Vet Solutions Stuff does not burn, it dries completely, AND it has aloe in it to soothe any irritation from the scrubbing and cleaning.
So the next time, when you go in to REALLY clean, get the treats out and let the dog know that you have them and are willing to dole them out for good behavior.
Hold to dog down, or get someone to help you, and use the vet solutions container to squirt into the ear. You can really get a decent stream from the container that it comes in, and you can just squirt it right in there. That will help loose a lot of the stuff in there on it's own.
Now, a dog's ear drum is something that you want to be aware of, but not be TOO worried about. As far as you can fit your finger inside the ear, you will NOT hit the ear drum. The ear drum is actually at a sharp right angle in towards the brain, so the ear canal will look like it just goes in a slight downward incline, but at the end, it takes a sharp turn. So as long as you shoot the stuff in the same angle as the ear canal, you will not damage anything.
When you do put anything wet and cold in your dogs ear, it will try to jerk away and shake it out. Wouldnt you? Just hold on to his and tell him that it will all be over in a little while. Once you are done squirting, you can let him shake it out if you want, just hold on to that collar so he doesnt take off. You're not done.
I usually use a Q-tip to clean my dog's ears, but you can use a cotton ball if you are not comfortable with that yet. I usually use about 10 Q tips on my dog! I just get in there and scoop out all the gunk, and you will be surprised and grossed out at the same time. If you use a cotton ball, you will not be able to get into the crevices as well, but its all what you are comfortable with. Wipe out as MUCH stuff as you can. You are going to want to do a second squirt with the stuff and let him shake it out again. You will probably see even MORE stuff come out. Clean again with your second round of Q-tips or cotton balls, and then just squirt in the medicine and dry him off.
THEN GIVE HIM THE TREAT!! Tell him how good he was and forget all about it.
If your dog runs every time it even sees the bottle, you can do some desensitizing training by just holding the bottle in your hand and giving treats. Walk around carrying the bottle and make it common thing in the house. Not something that comes out ONLY when its ear cleaning.
Honestly though, I do not suggest the use of any medications, as it usually does not NEED to be done. You just need some training to get your dog to know that it is going to be ok. Just like with kids who do not want to take their nasty tasting cough meds. You dont have to drug them to do it. WIth a little convincing, it can be done.
P.s.
I am not a "professional" however i JUST went through this with my beagle. He gets ear infections often enough that i feel like I am an expert. I also have a GREAT vet who will let me help with services like this so I can learn to do it at home. He let me see through the ear scope and showed me how the dog's ear canal was set up. Then, it was just practice.
Be firm, confindent, and loving and you will have no issues.
Ear infections can be very painful so being firm is not the answer but medical relief is.
Food allergies can lead to chronic ear infections so a PROPER food trial should be done for 8 weeks with z/d and no other food or treats or rawhides or oral heartworm preventions.
Nothing should pass his lips except z/d and water for 8 weeks.Your Veterinarian should supervise this food trial.
An opinion from a dermatologist may be your next step then consider surgery as a last step.