You should keep iTunes on your pod; it's the easiest way to get updates from Apple. However, I wouldn't use iT for anything else. There are a number of free programs that make it easy to transfer files to/from your pod, and to as many computers as you want. Most of these programs will sync on command, or you can select files to transfer. I couldn't find a free prog that transferred videos, but not a prob for you.

download.co m or other free software sites will have a few of these programs, and many people have reviewed them; all can be found via Google, etc. There are a couple of these programs that can be stored on your pod so that you can download from any computer you plug into, regardless of OS. I don't know about bookmarks, but there are probably free readers that will run on your pod. Find easy instructions on the web if you need to learn how to tell your pod to act as as a mass storage device.

As to your accidently hitting the switches, you could probably inprovise a small hard case. A shuffle would likely fit into a medicine bottle.