Thanks. What lots of folks run on here for speakers is the Polk DB series. They have a high sensitivity, ~92dB and are water resistant. I'd recommend them. It's strange because Kicker makes quality speakers, though I did notice the sensitivity of the 4x6 was 88dB, leaving something to be desired.
As far as a sub, I'd consider powered subs unless you are ready to fill your trunk area with a sub enclosure and separate amp. I have a powered sub 8" PS-8 by Rockford Fosgate. They take up less room. I've also seen recently a 10" powered sub, but can't recall the name as it was not a well-known brand.
As far as head unit, I'd suggest something like a marine head unit because they are water resistant and have a white background and black letters, which is much better for seeing the face of your head unit with the top and doors off. Convertibles often use these types of head units as well. When the time comes, just find out what you don't like about the Kenwood head unit, throw your findings on the forum and decide on something else.