Interesting concept. However, I am one who believes you should set your ipod up BEFORE you drive to avoid having to fiddle around with it.
Put it on a playlist you actually LIKE and just drive.
The FM transmission solution is not adecuate IMO. You should get a deck with an aux input (any one is probably better than the car's OEM deck).
I did that then got this mount
for my 3G ipod and my wife's 5G.
Cost: $7 apiece (amazon had them on sale, Electrogalaxy still does). It hooks up to the cars vent and you can see the ipods screen there (if you have to).
After Apple has sold 90 million of these things (21 million the last quarter), you would expect Detroit to do a better job of integrating them into their new cars. Aux inputs are now coming standard...finally.