First: You should know that I'm still on a PRS-T2 but crawling the web and the stores for the next system to move on to, since Sony left the reader market here in Germany, so...
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Something that matters though: how easy is to set up collections/shelves on both these?
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Are calibre tags important and do you use them to let the reader build collections based on those? Do you want to have multiple tags (e.g. Scifi, Action, Horror) per book and have the reader sort a book with more than one tags in several corresponding collections while plugged in to calibre? Then the Kobo would be better suited out of the box than the Kindle. Kindle doesn't "listen" to Calibre like Sony or Kobo does.
It would be cool to hear more about which specific functions the Sony has you use rather frequently while managing and reading your books.
For example, I love the fine dictionaries on my Sony - an aspect in which Kobo purely sucks. Kindle or PocketBook would be better here.
I love to tap a word here and there and push it over to Wikipedia, just to see what weird weapon, aircraft or other technical invention it is, that's going to determine the action to unfold next in the book. So I need a Wikipedia link next to the marked word, a WiFi connection that establishes fast and a fast and simple browser to load Wikipedia and it's images in a snap. Sony does that and brings me back to the book very quickly also.
How does a Kobo, Kindle or Pocketbook handle such a use-case?
The more I learn about other systems, the more I see just HOW perfect Sony did it back then. Haven't found a match I would swop the T2 for, but I think Pocketbook will come close one day. Since I like a warm light for reading, all the built-in frontlights are just shabby for my taste. The first display that came almost close to my T2 was Paperwhite 2, it was almost as bright and contrasty with it's light turned off and became annoying with the light turned on. The slight step in resolution was barely noticable from more than 20cm viewing distance. Kobo H2O makes a difference because the screen is slightly larger - I always hoped for Sony to go that route, but

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Good luck with finding the best system for you. At least, your T1 has a darker screen than the T2, which is a bit brighter and warmer, not the old cold grey. Current readers should be at least on par, rather better, to make for an upgrade as far as the screen goes. Other than that it depends on how you use your Sony. I'm still hoping to find something that's not a step back for me...