The first thing that annoyed me completely was the Outlook security message every time I tried to synchronize my Calendar and Contacts onto the iPod. This free utility allows you to choose "Always Allow, or Always Block, or Ask", for Outlook prompts, much like popular firewall products do. The only disadvantage is that Outlook has to be running for it to work (just put it in your startup).
http://www.mapilab.com/outlook/security/
Screen protectors that have no adhesive residue:
http://www.screenguardz.com/mediaplayers/
The next 3 resources are for all digital media fans.
The first one is the easiest way I've found to make MP3s out of all your protected content files without wasting a blank CD-R. It plays and records them on your computer's sound card. (Be aware the free trial only records a few seconds of a song.)
http://www.tunebite.com
If you are getting tired of your CD collection and need exposure to some new music, try this:
http://www.radiotracker.com
I use it to record the top 25 songs of my favorite genre, then transfer them to the iPod to listen to and decide if any of its worth buying. The songs that are recorded are not high quality, and they will have radio babble or fades in/out from other songs at the beginning/end sometimes. But its about the same as listening to the radio and its got the added convenience of pause/rewind. Plus there aren't any radio stations for my favorite genre here in my area, so I finally get to hear Alternative Music in Alabama.
:-)
If you've lost your computer's CD/DVD-+RW drive's list of manufacturer's recommended blank media, then you can go here to find out what each brand of media has been tested on:
http://www.videohelp.com/dvdmedia
If you happen to have a ReplayTV DVR, and DVArchive software, this free utility will make moving shows from ReplayTV to iPod Video (5G) very easy:
http://www.videohelp.com/tools?tool=MPEG_StreamClip
(I haven't figured out how to put a DVD on the iPod yet, but this utility is supposed to do it.)