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You won't be able to jailbreak any new Kindle, so collections will be out. There is a way like you said that I think still works by opening it up, connecting to a serial port, and much much more involved than how you did the PW1. The method you used is no longer possible and likely to not ever be possible if someone hasn't figured it out yet.
Kobo readers manage collections very nicely, you can set up Calibre to automatically put the books into the proper collections as you transfer them to the reader. You can also add your own fonts to Kobo readers (another thing you can't do with a Kindle). There's also better font adjustments on the Kobo where you can darken/thicken the font (again, not possible on the Kindle).
I have the Kobo Glo HD and I love it. Very even screen coloring, a bit on the softer/warmer side, and zero problems with it. I ordered mine from Chapters in Canada and the total price after the exchange rate was $120 ($129 for the reader, $15 shipping, CAD prices). You just have to decide if you think you need the water-resistance of the H20 or not, if it's worth the higher price for you. I've read outdoors in a slight drizzle and have gotten some drops of water on the reader without any problems. If you read in the tub a lot or at the beach, the water-resistant model might be a better choice for you, otherwise I'd save the money and go with the Glo HD.
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