A couple of things.
@JimmXinu, thank you for considering it. I know that you have spent a lot of time with this program in the past, and just having it is a wonderful thing, I wont bring up that suggestion again.
@Ryune, I can verify what JimmX says, overall Kindle is a great option. I also know that my kobo has issues in the past. I do still own a Kobo, so I can check mine at home in a couple days, when I get home, to see if it has fixed the problem, but I wont be able to until then. I'm not sure how long you're willing to wait.
Kindle has it's own little issues that annoy me, though not as badly as before. One big one that drives me nuts is when sorting books into collections (ie folders) if you dont have a connection to cloud (wifi), and sideload everything (as I do - I'm a bit paranoid and hate amazon knowing everything I read), you get an error about collections not syncing to cloud and a second error when you try to load them into a folder. Now, this used to be every time you did it, but they fixed it and now it happens every ~24 hours. It's still annoying, and I have found no way to bypass it. But once those books are loaded into a folder, it stays there and updates accordingly. Most of the time when I update a book it only takes a minute or two for my kindle to update (though that depends on how many updates I put on).
If you do get a kindle and are even remotely rough on it (I take mine with me everywhere, in pockets, bags and I travel a lot). I'd highly recommend getting a case as well, it's a worthy investment. And, if the new oasis (which I would love to have) has a similar screen to the older paperwhites and other ereaders, they can crack fairly easily (just a little pressure in a small location). This is the same with any ereader I've ever had - so don't think kobo's are any better - but I noticed when I put a cover on it it got less cracks in it from being toted around in my backpack, briefcase, bags, etc. Generally the cracks aren't bad but they can be disruptive to reading as its a bright spot on the screen. I personally plan on buying a 3 year warranty next time I get an upgrade (Probably Oasis2) along with a case.
I don't like that kindle has its own format, but that's not a huge issue with calibre. If you do get a kindle, use the AZW format, rather than the old mobi whenever possible. It's very similar to epub and can handle most of the newer formatting issues mobi doesn't handle well.
There are other small issues on the kindle I've run into that I don't like, but mostly they're minor annoyances, like trying to get you to rate a book whenever you get o the end (just close the popup), but it happens anytime you get to the end, so if you update a downloaded fanfic chapter and the index isn't long enough (when it's placed at the end of the book) when you get to the end it wants you to rate a book. As I said, annoying, but rather minor. There's also no other way to keep track of length of book on a device outside your kindle. If you transfer kindles it's a matter of finding where you left off in every book - not a hard thing if you've only got a few books and your old device, or if you have great memory. Not so easy with thousands of downloaded fics, and so many crammed in your head they tend to overlap in your mind. I've had to do it a couple times over the years and used to be able to transfer the kindle files onto the new one so it would pick up the old downloaded info, not so anymore. Plus filing all the books into different 'folders' is the same way. New device? do it all over again.
But, I still buy them. Despite there issues, overall I feel they're the best ereader option and stay with them.
Now that I've quit rambling, let me know if you want me to look at that Kobo when I'm back home. I'm pretty sure they've had several updates since I last used it, so I'll update the firmware and check about how they handle updated books.
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