With a couple of exceptions, it seemed to me when I was shopping for a HD recently, that the new regular - line bikes were strippers, and that it would take some serious coin to get them where I'd like them to be. So, I bought a three - year old SG Custom with 6k on the clock, for about 5 g's less than a new one. It had a couple of extras, but I added a removable windshield and a sissy bar backrest/luggage rack. Those few things added almost 1 g to the price - still a lot less than new. You'd have a hard time convincing me that a new regular - line bike, with the extras I'd want, is worth it.
The CVO's, on the other hand, might make sense if you must have new and want some serious upgrades that would cost you more than buying the CVO.