I think it depends on the ears. My floppy dog's ears need to be cleaned more often than the sticky-uppy
ears that my other dog has. I find that as long as I do it regularly, every few weeks in the case of our floppy dog, it's enough to wet a cotton ball and wipe out the inside of the ear (not too deep). I only do the "squirt and massage" with the cleaner if I'm seeing a large amount of gunk of suspect an issue.
Now during allergy season even my pointy eared dog needs her ears cleaned more frequently, but that is just due to the eye allergies and her eyes have extra discharge at that time too. I usually do it once a week then if I remember, just because there is so much gunk that an infection is likely if it builds up.
Normally I clean with a 50/50 vinegar/water solution unless we're having any issues that require a special cleaner or medication. For stuff that you're actually squirting in the ear (cleaner or drops) I've heard that it's less unpleasant if you warm the liquid first, say by letting the bottle sit in a glass of warm water for a while. But most dogs aren't really a fan of it - I just have DH help me hold them still or do it myself, get it done as fast as I can, and give a treat afterwards.