Here are my 2 cent equivalents:
You love your bike, why change it? If you've got the well known handling issue, upgrade it (e.g. glide-pro bushings, ohlins rear shocks, cartridge emulators up front) and it will handle better than a new one.
To me Harleys are about getting away from the all-too-common throw away mentality. I do not mean to flame anyone, just trying to explain why I truly enjoy my old bike. I could probably afford a new one, but why?
That old sled is not only my ride, she's also a keeper of loads of good experiences (and a couple of bad ones too, come to think of it...). I bought it in '98 while in Korea, and I've had her up to the North Korean border, down in Southern Europe, up in Northern Europe, etc. but unfortunately not yet over on your side of the pond (hope to do some day).
If you are really looking for a zen-like experience I can promise you it does not come through buying a new scoot. Get to know what you have, the sounds, the ticking, the little quirks. Buy a parts manual, a repair manual, ask questions, and do your own fixing (I'm not sure how easy that always is with new'ish Harley's, but anyway). Bottom line: Do what you want, but make sure it's what you want. YMMV