Looks good! My 2 cents worth:
I wouldn't paint it. What you have is in great condition. I never got the matte thing, but it's your bike after all.
The levers look fine to me. Tips even with the bottom of the drops is the normal starting point, and it doesn't look like you're far from that. I might rotate the bars forward just a bit, but not at the sacrifice of comfort.
If those shifters work for you, cool. I'd be inclined to look for some barcons.
Re: front brake housing - with aero levers I would use a headset spacer/cable hanger rather than the stem hole. Pretty minor point I know.
Street tires should make a big difference.