Apple has LONG had a two tiered product offering ... Macs vs iMacs, PowerBooks vs iBooks etc.
I just bought my fifth Mac computer (I'm one of those) ... and I have never regreted opting for their high end line. I'll be getting a 20 or 40 gig iPod, a Bose SoundDock ... and maybe those amazing Bose headphones.
LOL - you sound like me. I had the first generation iPod 3 years ago, upgraded that and then also got a mini last year. Now I have decided I "need" the shuffle. I use them all for different reasons - the big iPod mostly sits in the Bose SoundDock in the LR. The shuffle is the perfect thing for running, tho - lightweight and not susceptible to skipping as a hard drive would be. I don't need a display because I have a workout playlist for running and for the gym.