Replying to Weird boot pain - need advice

I've recently begun having this pain with my Full Tilts this season.  It happens on both ankles, one third of the way up on the outside of my calf, between the 2 and 3 o clock position on my right and 9 and 10 o clock position on my left leg.  It feels like the pain is in the tendons or muscles.  It gradually fades over 4 or 5 days but is re-activated after one day of skiing.

Before you jump to conclusions (should have seen a bootfitter, and so on):

- I went to a bootfitter and was fitted for the boots.
- The boots felt fine after I broke them in (3 days).  They felt amazing by the 5th day.
- The pain did not start until my 6th day of skiing this season.
- This is not shinbang (had it in my last pair of boots), it's more on the side of the leg.
- Hurts badly when I press on the area after a day of skiing.

My two theories are: after the liner packed out, the padding grew thin in the area where the intuition liner ends (the inside seam or whatever you wanna call it).  When I tighten the top buckle, I can feel the part where the buckle is attached to the shell press into my leg.  Whether the seam of the liner or the buckle/shell is to blame I'm not sure.
OR
I sprained both ankles at some point (as indicated by the tendon pain) from one of the many times I wrecked and every time I ski it aggravates the sprain as I haven't given it time to heal.

I will try to see a bootfitter in the near future but know there are some knowledgeable people on here who might have seen this problem before. +k for helpful answers.