Classic is the way to go for sure if press longevity is the only concern, but there is nothing wrong with the challenger either. Plenty of people use them and they work great. The quality of the ammo will be the same......
I have the deluxe turret, which is cast aluminum, vs the classic turret, which is cast iron. Basically the same as the two you are looking at only in turret form... Do I wish I had the classic turret? Sure, but my deluxe turret works just fine and makes great ammo. Someday I will upgrade to the classic, but for now, I have other things to spend the money on. The biggest peeve is of course the primer handling, I have just consigned my self to sweeping up primers after each decapping session....
Honestly, If I had to do it over, I would get the deluxe kit again and keep wishing for the classic a bit longer.