I was on the two year plan, maybe three years between new bikes for decades. When Harley came out with the CVO, it was all I bought. Six of them over the years - until I purchased a 2007 Screamin Eagle Ultra Classic. That was it for me. Almost hard to describe all the issues with this bike. And I had them all. Head gaskets, compensators, lifters lead the list. I couldn't even tell you how many times I have replaced the compensator or lifters. My 2000 FXR runs like a champ and is 100% trouble free. My 2007 SEUC, well I just limit the miles I put on it, and maintain it as necessary. I don't know if I will ever buy another motorcycle. I know I'll never buy a new Harley, and I know I'll never buy a used Harley from a dealer. Harley will not get another dime from me. I wouldn't rule out an older used Harley if I saw something interesting. Maybe a red flames 2002 CVO Road King? I was the dream Harley customer, until they abandoned quality and abandoned customer service. They would have been money ahead to take care of me as a customer, but they chose not to. But it's a game where the customer holds the ultimate power. I am quite certain I am not alone in my decision....
I'll probably never buy another either. Seven Harleys in 13 years, and we're at almost 20 years now, still on my '14. I'd love some of the features on the current FLHTKSE, but I won't buy one. So many things have been removed, but the price goes up and up. I won't pay that much for one.
The real killer? Wondering when it will break. If it breaks, how much to fix. The uncertainty of reliability spoils all the enjoyment. Listening to the motor constantly and wondering "Hmmm what's that noise?" For the same price, I could buy a pretty fully loaded BMW
car, and not have the same worries to spoil the pleasure of owning and driving it.