You definitely do not want a repaint if you can avoid it. You would hate to run the risk of the shop not matching the paint or getting the orange peel right or having to have them blend your rear quarter panels for that small area.
I fixed mine on my 05 by pulling out the rear light. After taking out the rear light, you will see three tabs that fit into slots in the bumper cover. When they heat up, one of the tabs lifts out of the slot. I went to a hardware store and bought a flat head self taping screw. I then drilled a very small pilot hole in the area near the problem tab (I think it is the tab furthest to the right), then screwed in the screw. As the screw goes in, you will see the cover pull back up into place flush with the rear quarter panel. Just be careful not to overtighten it, just get it snug. The chipped area will be hidden under the quarter panel and then all you have to do is re-install the rear light and you are done.

 

I did the same thing with a rivet gun, my bumper was annoying me too.

 

did you look over the contract? when you buy a lease sometimes they add like 5 grand to the total cost. Calculate your lease payments plus your down and add the final cost they are willing to sell you your car. it can be like 37? 38? just my experience. Not talking about the s2000.