you have asked a series of tough complex questions here, but i'll do my best.
if darden says to take the gmat again, and you want to reapply to darden, then you almost have no choice but to take it again. these evaluations are taken seriously when you call the adcom office. they are not telling you anything but the truth. the person on the phone probably looked at your file when spkg with you and it likely said, "needs higher gmat." since your M score is already excellent, it's likely due to your V skills. darden is a case study school, so strong V skills are critical. with a low V on GMAT, your essays need to be written perfectly to offset. otherwise, there are concerns.
as it relates to your strategy/planning, my advice is to do one thing at a time to stay focused. all the gmat work first, then all the essay work. or just decide you're skipping the gmat and head straight into essay work.
from your summary eval, it's tough to follow your accomplishments and any linearity with your career progress. this might be a reason for the denial the last time. it must be very clear (particularly for int'l apps) how you've moved from one job to the next with more responsibility, leadership, etc. based on your vitals, there's nothing that could be keeping you out of a top 10 program, except for perhaps this challenge.
hope that's helpful,
Former Kellogg adcom member, offering a new approach to MBA Admissions Consulting.