To answer your questions:
1. It definitely is a risk if you look like a "job hopper" or a dilettante who can't stay in one place for very long. Also, what really matters more than your job title or listed responsibilities is the impact that you've had on every organization. The more you move around, the harder it is to show a real impact on any one company/organization. So, I would say this is a potential weakness that you will have to present the right way. This is something that we help clients do all the time.
2. Your background is interesting but not so much that admissions officers will look past a so-so GMAT score or a confusing work history. I don't mean to sound discouraging, but don't overestimate how much one strength may overcome a weakness in another part of your application!
3. Even though you've been dinged by INSEAD, its Singapore connections make it almost a no-brainer for you try again.
4. Right now you should be fully focused on the GMAT. The CFA will only help you a small amount in getting into a top-ranked MBA program (and then getting a great banking job). I'd rather you get a 20-40 point better GMAT score than earn a CFA.
Veritas Prep | GMAT Prep | MBA Admissions Consulting | Co-author, Your MBA Game Plan
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