The best way to work things with the Kindle and a Sony is to purchase content in MS Reader format and use ConvertLIT to remove the DRM & also explode the content into it's base parts. That way you can do fairly easy conversions (without DRM) to LRF & Mobipocket for the same eBook. Calibre and Mobipocket Publisher do fairly pain-free conversions that you will enjoy reading.
Now, speaking of Calibre, you can use Calibre to download newspapers, bogs, and more web content. You can get a 505 cheaper then a Kindle and you will have the same Vizplex screen that the Kindle uses. That way, you will be 100% compatible with the 500. Have a look at Calibre and look are the forum at threads on Calibre or Libprs500 (the former name of Calibre). See what you find and then decide once you have enough information to make an informed decision. After that if you decide you still want a Kindle, go for it. But you might find you'll go for a 505. Only you can say. But please do your homework first.
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