Hi Dwarrel,
I'll try to answer your questions as best I can, though the answers may differ wildly from those that others might give. I can only relate about the DR1000, as I don't have any experience with the Iliad.
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Originally Posted by dwarrel
First off are these prices reasonable?
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The price for the DR1000s seems very reasonable. I don't think you'll easily find a cheaper one.
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Originally Posted by dwarrel
Does anyone have experience with using one of these two devices as a alternative to study books?
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I haven't used it for study, except for self study. So I have read a lot of textbooks (study books), but just for fun

In my experience the screen of the DR1000 is just big enough for most textbooks. With full-screen mode and a little zooming it's often quite readable. I wouldn't recommend a smaller screen than the DR1000.
The DR1000 doesn't compare well to real books, though, mostly because of its lack of speed. You can't skip through a book very quickly. If you're planning to use it in the classroom, you might be disappointed because of this.
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Originally Posted by dwarrel
Is there any information about how long most these devices last? (Like the first ipod generation had a reputation of breaking after 1.5 year, its a lot of money for me and since its 2hand i wont have warrenty.)
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Mine is about 2.5 years old. I can't say much about the reliability of the DR1000, though. It's always a gamble to purchase a device out of warranty. The screen is very breakable of course, so it also depends on you.
I've had one episode a few weeks ago where I thought for sure it was broken but then it slowly but completely recuperated from that. You'll probably have some scary moments with the device, but usually it's just for show

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Originally Posted by dwarrel
Do both devices run linux? And are they both evenly editable?
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They both run Linux. Can't compare the 2 in editability/hackability though. They are both no longer supported by Irex (since they've gone bankrupt), so you won't get firmware updates for either.
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Originally Posted by dwarrel
Do they have a bookmark function in wich i can quickly switch from page A to B and how many bookmarks are possible?
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On most pdf's it's very easy to create bookmarks, and often reasonably easy to use them if you don't use too many. I don't know if there's a theoretical limit on the amount of bookmarks, but I've seen behavior where the DR becomes very slow when using a lot of bookmarks (say 20+), though I'm not sure if this only happens with certain books.
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Originally Posted by dwarrel
Also any tips and advice about wich one to choose would be more then welkom.
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When choosing between those two, I would say go for the DR1000.
There might be other options though, like using a library, that might suit you better in the end.