Here's my very long list of iPod/iTunes improvements. It's a work in progress, and keep in mind I've only had mine for about 3 days, so I may have an issue with a feature that I don't understand totally well.

The formatting is slightly fubar, it looks fine in my text list but vBulletin stips my leading spaces, sorry.

iTunes and iPod improvements

Software - Itunes

o Allow multiple libraries - enable the use of multiple libraries within a single iTunes session / user login
* Enable songs to be "aliased" to other libraries so that they can be synced or played without having to actually copy the music file itself
* Enable backup of a library to another source as a library, and not just a pile of song files
* Allow right-clicking on a song and choosing "Move to Library..." which allows for moving to an existing or to a new library
* Libraries should be coherent entities, including all library specific preferences and DB info within the library store. This allows for moving a library and taking with playlists, preferences, play counts, etc.

o Preferences
- General
* "Don't change focus" - application focus will not change when inserting a CD, docking an iPod or other external behavior unless necessary (critical error) and "Allow focus change" - application focus will change with CD insert, etc events but will save all library positions and cursor positions when returning to the Library view. It can be annoying to insert a CD and be browsing the library and lose your cursor position.
* Auto undock - A preference to undock the player automatically either never, after auto syncing, or after a predetermined amount of idle time
- Burning
* Add fourth mode "Prompt" - prompt for CD burning mode (Audio/MP3/Data) at burn time.

o Ripping/Burning
* Allow multiple CD/DVD operations - if the user has more than one CD drive available, enable ripping or burning from multiple drives simultaneously.
* Allow a selection of songs in the library to be right-clicked on and then burned to optical media using the preferred method

o Checkbox Fields
* Expand the number of checkboxes available and specify their meaning
* "Don't sync to iPod" - Track will not sync to iPod, but will be playable on PC
* "Don't play" - Track will not play in any play mode or appear in a smart playlist. Track can be added to playlist that will be burned to CD, but won't be played if played in iTunes itself

o Playlists
* Expand the "Limit" function of smart playlists so that they can be limited by multiple criteria without affecting how many songs are in the playlist (providing the library can support the limitations and the list length simultaneously). Such as "Limit to N songs by the same artist/genre, limit to N genres".
* When clicking on a playlist, a fourth column should open in the browser to enable display of the playlist titles. Clicking a second time displays the playlist in current detail format, replacing the library browser
* Randomize order button/menu option - shuffles the contents of a playlist

o Miscellaneous
* On-screen display of the iPod's battery charge and charging status.

Hardware - iPod/dock/cable

o Player
* Soft locking - press and hold a key to lock the player's buttons, like the HOLD switch. A wheel/button/wheel combination unlocks, similar to a cell phone's keypad unlock technique
* Manual HOLD switch should be knurled or have some grip to it. Switch force is right, but the button is slippery.
* A more durable skin, like brushed aluminum. Skin should be a crush-proof shell.
- Bluetooth capability
* Bluetooth remote control, perhaps with scrolling display and possibly a jack for connecting earbuds
* Bluetooth headset capability for no-wires headphones
* Bluetooth sync -- slow, but for on-the-road syncing it would be great.
* A slim battery pod that attaches to the base of the iPod (in effect making it slightly taller) and holds two user-replaceable batteries. An idea similar to the Belkin, but the mounting would integrated better with the iPod case
* Accessory attachment suggests a need for integrated accessory mounting anchors (small threaded sockets for attaching clips, battery packs, cases, etc.)
* Adjustable touch sensitivity - default appears to be too high
* Better tactile feel for existing buttons and control surfaces. The wheel's turns in software could be synced with tactile bumps, for example.

o Dock
* "Undock" button - when pressed does the same thing as undocking the Ipod in iTunes.
* USB charging of the player. Player should ship with USB2/Firewire combo cable and it should charge the player on either bus connection.