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Hi Shane, welcome to MR.
You're gonna LOVE your new Reader!
As far as your questions go:
1) I would say that you belong to the VAST majority. Cases are an absolute necessity on your reader. As far as the Sony brand cases go, I find them to be well made and nicely fitting. I don't have the one with the built in light, but my mom does, and she swears by it.
Because your Reader has a screen, there will be some level of glare as light is reflected off of it. Simply adjusting the angle at which you hold your Reader will most likely deflect the glare until doing so becomes second nature to you.
2) I like the Kobo store much better than the Sony Store as well. As far as I understand it, (and no doubt if I'm wrong someone will be by to correct me) the ebook version does not necessarily have the rights to the cover image. The publisher just generates a generic one, assumes that that's acceptable and sells it to you.
Just one more tip for you: Learn Calibre. Calibre is the single most important piece of software for your Reader. Don't try to use the Sony software at the same time as Calibre either, they don't play nicely. (Actually, I don't use the Sony software at all.)
Merry Christmas and enjoy!
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