I have below my answers to your questions:
What can I do in the next 3-5 years to get into a Top 5 school? e.g. HSW, Columbia, Chicago, Northwestern.
The best strategy is excellence, in whatever it is you choose to do. Figure out what you enjoy, what you are passionate about, and then work like crazy to make a legitimate impact. Making an impact, going above and beyond, shifting the way things are usually viewed; these are all behaviors of people who are admitted to the very top business schools.
What is considered quality work experience? Promotions? Leadership?
Business schools are particularly looking for experience in managing and leading others.
Should I be focused on ECs I enjoy and that demonstrate business skills?
Focus on areas you are passionate; those will be the places you most succeed.
Should I retake my GMAT because of my low GPA and low AWA score given I have a few years before I actually apply?
If you can improve your score by a significant amount (40-50+ points), you may want to consider this. If not, there are other places on your application where time would be better spent.
Please let me know if I can answer any other questions!
Conrad and the Stacy Blackman
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Stacy Blackman | Stacy Blackman Consulting Inc | http://www.StacyBlackman.com | +1 323.934.3936
MBA blogger, US News and Author, The MBA Application Roadmap