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Copy music to iPod based on recent iTunes playback iPod
My iTunes library is much larger than the capacity of a 4GB (or even 8GB) Flash-memory-based iPod. Therefore I searched for a solution that would allow me to automatically copy a selection of songs I'm actually listening to over to my iPod. I didn't want to bother changing the playlist I am syncing with the iPod manually every week or so.

The solution was based on this AppleScript snippet I found on the Internet, with some changes to make it work the way I wanted it to work. The script adds albums to a playlist based on the songs I recently played. In that way, the iPod is always filled with the music I'm enjoying right now. 2br Here is the script:
with timeout of 1000 seconds
    tell application "iTunes"
        if exists user playlist "Copy to iPod" then
            delete every file track of user playlist "Copy to iPod"
            make new user playlist at folder playlist "Test" with properties {name:"Copy to iPod"}
        end if
        repeat with aTrack in (file tracks of user playlist "Recently played for iPod")
            set tempAlbum to album of aTrack
            --Make sure we haven't already added this album
            set testAlbum to count (every file track of user playlist "Copy to iPod" whose album is tempAlbum)
            if testAlbum = 0 then
                -- Nope, it's not in the playlist
                -- Let's check and see if there's room to add it
                -- Edit the next row (after: is less than) to set the maximum size limit. 15 GB for example is 1.5E+10, 7GB is 7E+9
                if (size of user playlist "Copy to iPod" is less than 7.5E+9) then
                    duplicate (every file track of library playlist 1 whose album is tempAlbum) to user playlist "Copy to iPod"
                    exit repeat
                end if
            end if
        end repeat
    end tell
end timeout
To use this script, you need to create two playlists: One smart playlist called Recently played (for iPod), with time-based selection limits (like the built-in Recently Played playlist), and whatever other conditions you want to apply (e.g. no audio books). The ability to add my own conditions is why I used my own version of the Recently Played playlist, instead of the provided version. The second playlist is a standard playlist called Copy to iPod. The Copy to iPod playlist is the one that will be synced with the iPod.

The major drawback is that you have to play a song first in iTunes (playcount must be raised) before the album containing the song will be copied to the iPod.

[robg adds: I haven't tested this one. ]
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Restore iPod games from your iPod iPod
My Mac's hard drive was getting errors, so I decided to make a fresh backup and then reformat, reinstall and restore. Many of the files that couldn't be read were in ~/Music -- no problem, I thought, it's all on my iPod anyway. Getting music and video from the iPod back into iTunes is easy. Just disable syncing, enable hard disk use, and open everything in iPod_Control » Music » F* on the iPod (make sure 'Copy files to iTunes' is enabled on the Advanced tab in iTunes' Preferences).

Unfortunately that does not include games.Those can be found in iPod_Control » Games_RO, but they're not in a format that iTunes understands. There is one directory for each game you've installed. The directory is a number, but you can find out which game it is by looking in the game's Executables directory. To reinstall your games, all you need to do is create a zip file of each game, and then set the zip file's extension to .ipg. For example:
cd iPod_Control/Games_RO/18000
zip -vr9 ~/Desktop/"Sonic The Hedgehog.ipg" *
Now you can double-click on the file and iTunes will load it.
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Use VPN on the iPod Touch to read Exchange mail iPod
With Apple's Mail included in the software update ($20) for iPod Touch firmware upgrade 1.1.3, I was looking forward to really improving the utility of the device by reading my work email. However, the comments I read on the net said that the iPod Touch didn't have the networking preferences like the iPhone, and thus, VPN couldn't be done.

But they were wrong!

VPN is hidden in Settings » General » Network, and if your company's Exchange server has IMAP services activated, then you can configure the iPod Touch to read your work email. The only problem that I have found is that the VPN connection isn't persistent. If your iPod goes to sleep, the VPN connection drops out. Go back to settings to switch it back on again. Now I have full email wherever there's Wi-Fi.

[robg adds: This is the same spot where you'll find VPN settings on the iPhone. I assumed this was documented in the updated iPod Touch user's guide, but it doesn't seem to be mentioned anywhere.]
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Extend 24 hour movie rental period on iPods iPod
This works at least on the iPod Nano, though I hope it works on the Mac as well. If you start to watch a movie but do not finish it and the 24 hour period is running out, just start the movie playing on the iPod and press Pause. The movie will remain playable until you close the movie -- even past the 24 hour time period. When you finally decide to stop the movie, you will receive a warning from iPod that the time has expired and will be prompted to resume watching or delete the movie.

[robg adds: During Expo last week, I wrote about my concerns with the 24-hour limit. Yesterday, my colleague Chris Breen stumbled on this same solution to the problem. Chris notes that you must choose one of the resume or delete options when you go back to the iPod; he force-restarted his iPod just to see what would happen, and found that the movie vanished. For me, the key question is whether the Apple TV will also support this feature or not, as that's what we'll be using to watch our movie rentals. Until the software update is released, however, that question will remain unanswered.]
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A solution for iPods not synching in iTunes 7.5 iPod
I recently bought a new iPod classic to replace my 5G (with video). After setting up the iPod, it refused to sync automatically with iTunes as my 5G had -- it would eject within seconds of being connected, so I had to press Sync immediately to get it to sync.

Last night, I got bored and went to poke around in the Preferences. Lo and behold (in iTunes 7.5), the iPhone pane has turned into the Syncing pane, and there's a checkbox with the text "Disable automatic syncing for iPods and iPhones." Unchecking it solved all my problems.

[robg adds: When I first read this, I thought it was one-time occurrence, as none of my machines have had this box checked by default. However, three additional hint submissions on the exact same subject make me suspect that something else is going on, so in case you've been having auto-sync issues, here's the solution.]
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Take notes on an iPod touch iPod
Many users have complained about 'missing' features in the iPod touch, like an email application, the ability to add entries to the Calendar, and a note taking application. Until the iPod touch is 'hacked' to allow the installation of third-party apps, or for those who don't want to hack the iPod touch, it is possible -- and not entirely inconvenient -- to use the Contacts database to take notes that are then automatically uploaded to the home computer when the iPod touch is synced.

What I do is create a new Contact with a number for the first name and A for the last name, so it shows up at the top of the contacts list. Then create a new field in the contact named Notes and type away. It will probably hold as much as you're likely to want to type with the iPod touch's keyboard. When you next sync the iPod touch, the note(s) will show up in your Address Book, in whatever folder you have designated in iTunes. The default new folder is named Added.
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Recover a corrupted iPod iTunes database via copying iPod
I don't think this is a common occurance, but if it happens to you, it can be really annoying. Something indeterminate happened to my iPod, with the result that when it was connected to iTunes, iTunes popped up a message saying that it could not read the contents of the iPod, and that I would need to restore it.

okay, all well and good, except that disk mode still worked, all the files were there, as well as all the music in /Volumes » iPod_name » iPod_Control » Music, in its requisite F00-F49 (there might be more or fewer folders on different iPod models; I'm not sure) folders. Needless to say, with a total of 11GB free on my laptop, and 22GB+ of music on my iPod, I was not looking forward to copying back and forth more files than I had room to move, nor did I want to buy another hard drive just for this purpose.

A web search turned up nothing appreciable, except that people seem to post about this often with PC formatted iPods, and that nobody had a solution other than copy all files, restore firmware, copy back. I found, however, that when I removed the iTunesDB file from /Volumes » iPod_name » iPod_Control » iTunes, the error did not crop up in iTunes. However, there weren't any entries under the 'music' tab, as I'd removed the iTunes database file. That pointed to the culprit, but what was the solution? Here's what I came up with.
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Use a Mac instead of an iPod as stereo system source iPod
I ripped a number of my CDs using iTunes' Apple Lossless encoding for maximum fidelity. When I played songs back on my stereo system from my iPod, the music was thin and reedy, but when I played the same music back using iTunes on my computer, the music sounded virtually as good as from a CD player.

I assume that the digital-to-analog circuitry in the iPod is not nearly as good as those on my computer, so the same music sounds much better coming from the computer than from the iPod. Since I like to listen to music while I'm working at my computer, using iTunes on my computer as jukebox source is a no-brainer. Just plug the headphone jack into a high-level input on your stereo. I use a 17" G4 Powerbook; your mileage may vary.

[robg adds: I'm running this hint in order to see what others think: I've never actually used my iPod connected to the stereo, and was curious to see if others have noticed a definite audio quality difference between an iPod and a Mac as the music source on a stereo system. Share your experiences if you've tried both...]
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Recover space on an iPod iPod
I was recently wondering why there are so many "other" files on my iPod: you know, when you connect the iPod, you see a graphic at the bottom of the iPod Summary window in iTunes showing what kinds of files you have: music, video, photos, other. For some reason, it seemed to be much more than it should have been. "Other" contains your album artwork, any files you have on the iPod if you use it in hard disk mode, and games, but it seemed that the space used was excessive.

So, with Terminal, I started rooting around. (The iPod should be in hard disk mode to do this.) I found the following folder:
/Volumes/Dark Star/.TemporaryItems/folders.501/TemporaryItems
which contained a whopping 300 MB of files, named "Temp file 1", etc. I deleted these files, and recovered a fair amount of space.

To find the appropriate folder, replace the part of the path following Volumes with the name of your iPod, then, if you are not the first user on your Mac, look inside the .TemporaryItems folder to see which folders it contains. User 501 is the first user created on your Mac; 502 is the second; etc. You may need to check several folders, if you have used the iPod as different users. After you have cded to the appropriate folder, you can type open . to display its contents in the Finder and delete the files by moving them to the Trash and emptying the Trash.

It seems that these files are created during syncs, perhaps when something goes wrong or when you disconnect the iPod too early, but even after I deleted them once, I looked soon after and found more files, though I had not aborted any syncs. So, you might want to check this whenever your "Other" files become larger than you think they should.

Note: after writing up this hint, I checked on my son's iPod, and found he had no .Temporary Items folder. I then asked my buddy Doug Adams, and he didn't have one either. But in both cases, the iPods hadn't been used in hard disk mode. Checking an older iPod mini, I found a handful of temp files, much smaller than on my 80 GB iPod. So it seems these files have something to do with using the iPod in disk mode. Check your iPod and post info in the comments.
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Prevent iPod Shuffle from reverting to start of playlists iPod
My iPod shuffle would occasionally behave strangely on start-up -- rather than resume play where it was when last powered off, it would resume play where it was when last powered on. That is, if I had listened to three hours of music yesterday, it would start at the beginning, not the end, of that three-hour block today.

I eventually discovered that this behaviour occurs if the Shuffle is paused, then left alone until the green light stops blinking, then turned off. Turning the iPod off immediately produced the expected behaviour. Since I don't imagine it is a frequent occurrence to want to "rewind" the iPod in this way, I mention this not so much as a hint, and more as a suggestion for what to be sure not to do, if you're absent-minded like me.
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