A person with tubes through their eardrums would not need to equalize, because there would not be any pressure differential. This kid has had repeated ear infections, which is why they put drainage tubes in his ears in the first place. This is most likely due to some malfunction with his eustachian tubes, a not infrequent childhood problem, which most people mature out of.
If he uses a Pro Ear mask he will be able to keep his ears dry. The mask has little tubes connecting the earcups with the lens chamber over the nose and eyes. As you exhale through your nose, air travels out to the earcups and pressurizes them too. It is possible to partially flood the mask yet keep your ears dry because the tubes exit through the top of the mask. It is likewise possible to purge the earcups, should one or both flood, by pushing against the top of the earcup and exhaling through your nose. If this kid has to totally flood or remove his mask underwater, for some training exercise, then his ears will get wet and he could get water in his middle ear resulting in an infection. This should be explained to his DM who can alter the mask removal/purging exercise to a partial mask flooding/purging exercise.
If he combined the Pro Ear mask with Doc's Proplugs, then he would have a better chance of keeping his ears dry. That is of course providing he doesn't dislodge the Pro Ear Plug if the earcup should be displaced underwater.
Doc's Pro Plugs have a small hole in the middle of the plug and are made of flexible silicone. They create a small air chamber between the earplug and the user's eardrum. They flex inward as pressure builds, compressing that little bubble. Surface tension keeps the water from entering through the vent hole down to about 20 ft./7 m. With a pressure differential above 20 ft./7 m. some water can enter the air chamber. The key here is that the water exchange is extremely limited. This reduces ice cream headaches from cold water. It also reduces the response to water entering one's ears, which can make equalization more difficult.
If a person had a functioning eustachian tube, even with a perforated eardrum, it would be possible to keep an ear dry while using a Doc's Pro Plug.
If the kid's eustachian tubes are working now, he might be able to dive, but he really should have the tubes taken out first, IMHO.
I have used both products. I have had a reconstruction of my right eardrum necessitated by scarlet fever when I was six. My reconstructed eardrum is more delicate. I even suffered a reverse squeeze pin-hole leak once, but I healed. Doc's Pro Plugs and ultimately the Pro Ear mask, let me continue diving more safely and comfortably.
