After how many "descents" / repetitive dives do you run into troubles? From what I have seen everybody at some point reaches a limit sooner or later. If you feel equalizing is more troubling for you than others and are sure it isn't bad technique it might be worth visiting a doctor.
In my case it turned out to be a mild allergy/irritation which was fixed by something as simple as a nasal spray.
I found that the mask did help a bit minus the leaking issues however i noticed more problems clearing the second week. Finally went to an ENT and sure enough its allergies. Makes sense now considering i ran out of nasal spray at the beginning of the second week of dives.