Yes, I had 7 years of ankle pain. I've broken my ankle, snapped off my OS Trigonum, had it surgically removed, snapped my ligaments, etc. I've probably sprained my ankle 50 plus times from soccer.
The first step is to realize not all orthotics are created equal. Unless elderly, you should never have a post! Second, the method matters. You want the old school method where you stand on flexible material. Casting is often done when you are not in a natural position. Third, they should not provide too much offset if any on their own.
Finally, it's my opinion that good orthotics should be used to get you out of pain. Once out of pain, it's up to your body to prevent future pain. Your issues are probably from lack of flexibility and strength. Staying in orthotics forever prevents those muscles and the motion needed to do it on your own.
I also worked for the largest footwear company in the world. I've been filmed in every shoe we made. I could probably talk for days on the subject.