Well, I took the plunge and bought an iPhone after much (too much) deliberation. I decided not to wait for the inevitable 64GB iPhone or whatever the next generation might bring, and I have not been disappointed. The deciding factor for me was when I realized that I probably only actively listen to about 5-10GB of my music collection with any regularity. We'll see if that holds true.
The first order of business of course was getting a case to protect my investment. I had trouble deciding whether to get a hard or soft one. Why compromise? I settled on the hard and soft SwitchEasy RebelSerpent and I think that it's pretty dang cool. It has a perfect fit, gives great access to the iPhone controls, and feels great in my hand. I found it on iPod Lounge, which is my de facto source for iPod accessory recommendations. This case and another from SwitchEasy were their #1 and #2 ranked cases, so I figured I couldn't go wrong.