Does anyone mind articulating why wrapping the untapered portion of the striing around the post will break it? (or just any reason why it's bad?)
I've had strings break like this, and what has always made more sense to me is that it's the core that breaks rather than the wrap (as the OP suggested)—and the wrap is the only thing holding it together. The only correlation that I believe I've noticed with this phenomenon is yanking around on the string too much. I always figured: if you bend the string too much and it gets weakened (like bending back and forth those "unbreakable" black plastic combs), then under tension it can lead to that kind of catastrophic failure. IME, some string materials are worse than others..cobalt seems to be the most susceptible.
Like the OP, it's happened to me when bending the string before installation. It's also happened to me at the bridge if I set the witness points too hard. Sometimes the tone of a new string is just not as good as others, and I've been wondering if the same thing might be happening but just not so much that it breaks the core.
I've never had any trouble wrapping the untapered part of the string around the post. (probably never more than half a turn or so fwiw).