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I recommend registering - it unlocks a bunch of features as mentioned, plus gives you the ability to buy from amazon and download via whispersync. You can still sideload all the books you want (that works just fine - I do it all the time). If you want to check out books from the library, that likely required registration as well.
I have never seen the attraction of jailbreaking a kindle... it's such a limited device... though if you want your own screen savers, etc., I guess that's what you need to do.
If you don't like the special offers, just never use wifi (they time-out, then you get one of the plain backgrounds with a note to connect to wifi) or pay the $20 and be done with them (that's what I did). I normally have wifi off (device in airplane mode) unless I need to download something. I download and copy over the updates from amazon over USB which works just fine.
If you don't want what Amazon adds onto their devices, there are other devices out there (e.g., Kobo) that are definitely worth a look
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