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That doesn't sound normal. My copy of Reader isn't bugging me to update. In fact, as far as I know, Microsoft hasn't updated the software for a few years now. Heck, I've even forgotten the log-in credentials I used to activate it so I remove DRM from every purchase and keep DRM-free back-up copies in case the PC where I installed MS Reader dies or something.
Assuming you still have access to your ebooks, what I would do is use ConvertLIT to remove DRM from the ebooks (don't explode to oebps, just remove DRM). Then, uninstall Microsoft Reader completely from your computer. Don't know if it leaves any traces but maybe you should do a search or something to remove all traces of the program. Then just download the latest copy from Microsoft's website, do a clean install on your PC and activate.
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