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I went to a community college for two years and one of those years I withdrew from all but one of my courses halfway through the semester.

I was passing all of them with A's, but I had the opportunity of a lifetime to work full time on a congressional campaign in the fall of 2006. I talked to my professors and withdrew from all of the courses according my schools policy, which is that if you withdrawal with a passing grade it is not considered punitive and appears as (WP).

I then went back to the same school (the next semester) and retook every single one of the courses and ending up getting As in all four of them. My GPA at the community college was a 3.58. I then went to University and currently have a 3.99 average here, with the two averaging out to a 3.8 LSAC GPA.

My question is: will having 5 W's on my transcript hurt me? Should it be something I address in my personal statement? I have nothing below a B on my transcript. I can only imagine that good students leave school for a semester all of the time.

Doesn't sound like a big problem to me. Just mention that you withdrew for a semester to work on the congressional campaign.

Same as above. Attatch a seperate adendum, they shouldn't care. If you had W's throughout your transcript it might reflect poorly, but I think given your respectable GPA that its fairly obvious what happened.