Q: Is it possible to upload photos manually to my iPod 80 GB classic? I manage my music manually, but every time I sync it with my iTunes library all of my old photos are deleted.
A: Unfortunately, there is no “manual” sync option for photos. Your photo collection is always synced automatically based on the photos stored in the folder or photo album that you have configured to sync with your iPod via iTunes. In this case, whenever you sync your iPod with iTunes, the photos on the iPod are compared to the photos in your photos folder, and any photos that you have removed from your designed photo folder or album are removed from the iPod, in much the same way that iTunes handles music when in automatic sync mode.
Basically, iTunes expects you to leave your photos on your computer and leave iTunes itself pointing to a main photo library folder or photo library application (ie, iPhoto, Adobe Photoshop Elements, etc), and as long as photo sync is enabled, iTunes will check this folder each time you connect your iPod and match up the iPod’s content to the content of the photo folder or album.
If you simply want to load a static set of photos on your iPod and keep them there, however, you can turn off photo synchronization entirely in iTunes and leave the photos on the iPod itself. When you disable photo synchronization for your iPod, iTunes will ask you whether you want to leave the existing photos on your iPod or remove them:
Simply select the “Don’t Remove” option and iTunes will leave the existing photos on your iPod, but will no longer both to sync or check them against your photo folder on your computer. Note, however, that this is not a true manual mode, but really just leaving your photos behind after disabling sync. If you ever want to sync any additional photos onto your iPod, you will need to turn photo synchronization back on, and ensure that any existing photos are also in the proper location, otherwise they will be removed from your iPod once you turn photo sync back on.
One other option if you find that you regularly need to add and remove photos from your iPod is to check out the third-party application CopyTrans Photo (Windows only, $30, trial available). This tool will allow you to copy and manage the photos on your iPod without using iTunes at all. In this case you would simply disable photo sync entirely within iTunes, and use CopyTrans Photo instead.
More information on managing photos on your iPod can be found in our Complete Guide to Displaying Photos on iPod + iPhone.