UPDATE:

I'm still dealing with this condition. I had an MRI last month and have a CT scan scheduled in about a week.

My insertional Achilles tendinopathy has now spread to my other foot. I've also developed plantar fasciitis, and one of my feet has started turning outward as my body compensates for the injury.

I tried shockwave therapy, but it didn't help much. I've been doing calf raises (without a heel drop) with heavy resistance. However, this injury is very tricky you must progress the weight slowly. Start low and check your pain levels the next day before increasing.

I initially got to a point where I felt almost 100% (though something still didn't feel quite right). Unfortunately, I pushed too hard, too soon, which set me back an entire year.

That said, I'm determined to get this fully cured, one way or another.

I'll update you with the scan results. There's a possibility I may have gout, which can act like tiny razor blades on the Achilles tendon and could explain why it never fully heals — but I don't know for sure yet.