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You have some options, but I don't think any of them can do everything you want. If you want BookShare, you can use an Onyx Boox device, which runs Android and thus can use BookShare for Android. Be aware though that many mobile applications are not designed for e-paper displays, so if BookShare forces you to use fancy page-turning animations and such, it may look pretty ugly. Onyx devices are not waterproof, however.
Kobo devices have OverDrive support built in, and you can also read CloudLibrary books via ADE. They also offer waterproofing, but they can't use BookShare.
Since you need a large font size, what size e-reader are you looking for now? You can fit a lot more content per page if you go for an 8 or 10" model, but larger devices are also less comfortable to hold.
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