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Have you tried using SplashPhoto from SplashData? It includes a desktop program so that you can manage your files on your computer before you sync them to your Pocket PC.
The other way would be to just open up ActiveSync, click on Explore, then browse to your My Pictures folder within My Documents and drag and drop your images in there. Make sure you have enough room on your Pocket PC! If not, I'd recommend getting an SD card!
Another great application for viewing and even editing your pictures on your Pocket Pc is SPB Imageer.
Spb Imageer is a very powerful imaging engine designed specifically to streamline common processes that Pocket PC users perform with digital photos. Equipped with an incredibly rich set of features, Spb Imageer will make your work with images fast, comfortable and joyful. Even if you edit an 11 megapixels photo!
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