I had 3 Ws on my transcript, 1 for Calculus II, and 2 for an electric circuits class I had to take for my major (chemical engineering). I retook the Calculus at a different school (but not a CC) and I retook the circuits class at my school because they wouldn't accept the credit from anywhere else.
As for how this looks on the application, I can't say for sure but I got into two schools this year. I tend to think that medical school admissions is really about the entire package, most medical schools are willing to overlook a few Ws if your overall GPA is still within the range and if your MCATs are decent. However, at one interview, I was specifically asked about the Ws (Syracuse-I'm on the high priority alternate list).
As for retaking the class at a CC, if you're doing that because of financial or geographical reasons, what can you do? If you're doing it because you think it'll be easier, I'd rethink that. Half of the Biological Sciences section on the MCAT is Orgo, so if you're going to learn it, might as well learn it well, it'll help you in the long run.
Just my own experiences, hope that helps a little.