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Yeah, the 6 files per page is a limitation that a lot of users complain about. iRex has released the code for the content lister recently, and it wouldn't surprise me if there are already open source developers working on new versions to fix that (in fact, I know there are).
In the mean time, keep in mind that you can also create a directory structure. You don't have to have all 300 books on the same level and have to navigate through 50 screens to find them. Usually what I'll do when I move ebooks to my iLiad is create a directory for the series, and then move all the books for that series together into their own directory. That way when I start out the content lister is showing me each series as an item, and then I can click on it and get to the individual books. That way I'm not navigating through everything at once. I believe you can do multiple levels of directories that way. In your case, maybe break it down to something like a directory for each Journal, and then inside that directories based on issue or date, etc.
Regarding WiFi being slow, there is a known problem with transfering files via WiFi directly to the CF card on an iLiad. If you're using an MMC/SD card or the internal memory, then it shouldn't be as big of a problem.
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