The only thing I've seen that is easy to use with a case are the ones that leave the click wheel exposed that claim ease of using with the case (you DO remove the case partially from the iPod to use the dock) and the iPod armor... On that case (I feel I can relate to your question since I basically keep asking myself the same question) you remove the pod from the armor and just plop it in the case. The iPod armor seems like the best solution for someone who wants to use the dock every now and then but yet wants to protect the pod IF they use it mainly in the car, etc. But for someone who runs around with their pod, the skin seems more convenient... I am undecided but since my iPod photo is paired with my Alpine h/u and is locked in my glove box most frequently, I am leaning towards the armor or just the cloth case even that the iPod came with as I rarely need to clip the thing on myself and I have had three iPods in under two years, upgrading each time a newer one comes out... SO, makes me wonder if I should even be as obsessed over this issue as it is!!! Make it stop!!!