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Should I ask my doc about ear tubes?

So I love to travel and usually do maybe three times a year. I have a HORRIBLE problem with horrendous eustachian tube pain when descending. I was born 11 weeks early and had some ENT development problems but met the normal "checkpoints" after 18 months. I have asthma and seasonal allergies, and I've had both my tonsils and adenoids removed. I have seen an ENT specialist for the surgeries but not for this specific issue.

In terms of the preventitive measures, I take a regiment of Sudafed for 48 hours before I fly and have prescription Nasonex that I take for allergies to keep everything open. I take a daily antihistamine (Zyrtec) and have my inhaler on me at all times (even though my asthma is exercise induced). I take a Sudafed and a squirt of nose spray about 15 minutes before descent and begin to chew gum, yawn, pop my jaw/mouth, swallow (etc) to try and keep them open. I am always perfectly healthy when I fly bc I don't want to get others sick.
Nothing has worked.
I have had this problem since I was born. I am nearing 18. I've flown at least 75 times in the course of my life, one way or another. And there hasn't been a time where I haven't had this pain when I fly. Not once.

I know that either short term or more permanent ear tubes are an option for those with chronic ear pain/problems, but does it sound like a good option for me? If it is, should I go through my regular doctor or contact an ENT specialist?
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