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I'm a big fan of DropBox, every time I get a new ebook, I let DropBox sync it to all my computers. There's no DropBox app for the Kindle, so I manually copy it to my Kindle 3, and leave it there. I have over 1600 books on my Kindle. I never delete anything, and I still have plenty of room to spare. The whole reason I got the Kindle was to always have my library with me. I like not having to wonder if I have a particular book with me or not, I just do.
Included among those books are the MobileRead and Feedbooks guides, so I have access to those catalogs anywhere I have a connection, plus I can use the internal browser to surf over to Gutenberg and download their stuff.
If you absolutely must have DropBox running on the device, then as someone else already pointed out, maybe a tablet might be more suitable. There's also smartphones, I run DropBox on my Android phone, so I know that works. I'm not sure about other platforms.
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