I don't have much personal experience with the Achilles issues, but based on what friends have told me it is something that I have been pretty scared of getting and one of the reasons I eventually stopped trying to transition to zero drop shoes. (nothing against zero drop shoes, I just never could get past mild Achilles discomfort and didn't want to push it.)
I know others have suggested that if you have achilles discomfort, to avoid hills and speed work but more importantly take it easy and even seek medical opinion.
I run through all kinds of nagging pains and annoyances, but Achilles is one of the areas that you don't want to mess with as it could sideline you for a very long time as Alex mentioned.
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Couch to ??k - From the couch to a Marathon in roughly 18 months.
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