Can bilateral achilles tendinosis pain move up into the calves as the tendons heal? the tendon pain has improved but high calf pain has worsened.

No, thats very unli-: Kely. You probably developed some other problem, depending how you were treated for tendinosis. Possibilities include muscle tears (unlikely that you have it on both sides); clots (again very rarely do they occur on both sides); weakened muscles in the calves, if you have been treated by resting them for more than a few days ; now they are hurting, as you start getting around. See an orthopod.

Possible DVT: Which is a clot this is a medical emergency and you must inform your doctor of this or go t the er to have it checked out. Always better safe than sorry. If it is a clot you can get a pulmonary embolism and die. Get it checked out!