I don't have much experience than yours , I've only been playing for about 7 or 8 years , but I can asure you that the strings should never break if they're new .
I play .010's gauge , and they never broke before a month of heavy playing , that's why I make sure when I go giggin' that my strings aren't more than a week old .
I also use my Floyd Rose whammy to bend as far as it goes , and I never broke a string this way either.
I don't know if heavier gauge can stand much more heavy bending without breaking , but Malmsteen for example uses .008's gauge and he does a lot of 5 fret bendings and he never break strings during a show , but I remember that he said something in an interview about changing his strings daily .
Bottom line : It's non-arguable that the heavier you bend the shorter the strings will last , but isn't that what they're made for anyway ?
[Edited by SLY on 01-27-2004 at 10:37 AM]