AMCAS asks if you've applied for a specific school before when you add them to your application, not whether or not you've submitted an overall application before (unless they've changed it in the past year and a half).
Being a reapplicant was a big part of my application, so I made it rather clear to all my schools that this was not my first time applying. I did so because getting rejected the first time forced me to look outside the world of physicians and look at other careers, and I ultimately decided to come back and apply for medical school again.
How you're looked at will vary hugely from school to school. My current school had no issue with it... they've interviewed people again this year who were waitlisted last year (this was no my situation, as I I had not applied to this school the first time).
Another school I applied to waitlisted me the first time I applied, and accepted me immediately the second time. Another school I applied to rejected me both times post-interview. Another school interviewed me the first time I applied and waitlisted me, then didn't even offer me an interview the second time.