Before I stopped riding on the street, there was a Harley FXDL (Dyna Low Rider) and a Ducati 900ss in the garage. Both excellent bikes, just designed for different things.
I really liked the Harley. I grew up with them - Dad rode Harleys, Grandfather rode harleys, etc, so I always wanted one. And the new motors (TC88) are pretty reliable, there's not really any major probs with them at all.
However .... if I were to do it now, I'd put something custom together instead of buying one from the Motor Company. Buy a frame, S&S motor, etc ... nothing flashy or over the top, just a nice, unique bike, and it would cost less (or at the most, the same as) a base-model Harley.
Oh ... and the V-Rod isn't a Harley
We maintain a track-day bike for the GM of a rather large Harley dealer - he says he sells 2, maybe 3 V-Rods a month (they sell about 200 bikes a month out of their store). It's basically the Harley designed for the Japanese bike fan, or the younger buyer. He also says they *never* have problems with V-Rods (Porsche designs a good motor I guess