Okay, the results are in!
First off, here's my car in its usual parking spot:  
 
 It's 11:00 AM. I park facing east, and as you can see, the trunk will be baking for the rest of the day. 
Here's inside the trunk (That cooler sat in the garage for a long time. I should have dusted it off before I took the pic! 

 ) :  
 
 L-R: GHB and wide-brimmed hat, Cooler, Toolset and junk bag, unused floor mats, and reusable grocery bags.
And here are the results:
     Trunk     Cooler    Outside*
M    120/**    94/**     95/67
T    128/80    96/87     99/66
W    135/82    97/90     102/68
Th   137/84    94/89     106/68
F    137/86    97/95     106/73
Outside temperatures taken from US Weather Service reports.
*My car is garaged at night and doesn't experience the full low.
**I forgot to note the lows before I hit reset
As others suggested, a cooler doesn't prevent stuff from getting warm, it just smooths out the curve. What I didn't realize was that meant it would also delay things cooling off!
I've had four .7L bottles of store-bought water in that cooler for two weeks (along with 2 1L bottles in the GHB). I cracked one open just now, and other than being tepid, it tastes fine. I intend to continue that over longer and longer periods, to get a feel for how long I can leave water in my trunk.