Bought my first CVO, an 09 SERG because I had much more money in my 03 Fatboy with add ons, and it was still worth the same as any other 03 Fatboy.
So, the 09 SERG got traded in 12 with 43K on it for a 12 SERG. I had about 3K in upgrades on the CVO. It was very cost effective to trade for the 12 SERG. So in 15 I traded the 12 with 45K on it for the 15 SERGU. Again it was a cost effective trade as I added less than 3K in accessories, and I got a very good trade offer on it.
I should do really well on the 15 when I trade it as I will have about 2K in upgrades on it.
So, if you like all the chrome, nicer paint, nicer wheels and so on, and trade often CVO for me is a much better way to go.
I like having all the nice wheels, paint, chrome and power. So I would loose much more, adding it all to a regular bike, then trading in 2 to 3 years with 45K on the bike.