OK, here's an interesting way to think about the issue. Suppose the worst consequences of unbreakable DRM were true, that you end up only being able to keep your ebooks until readers and formats change and after that you have to re-buy in the new format. A scenario that's extremely unlikely in the real world even if the impossible unbreakable DRM existed IMO, but let's assume it for the sake of argument. So, what then?
Well - you see a new book. It's priced at X, you know that formats change about every N years. You also know you want to read this book and if it's good you may want to re-read it.
So the question becomes - am I willing to pay X for this book, knowing I'll get N years out of it? And if I end up wanting more I'll have to pay. And the point is - for most books there is a value N and X where the answer is yes for most people. And guess what N and X are under the control of the ebook vendors. So they can make sure that they are at a value that works for most people (in order to maximise their profits).
In reality N will always be presented as infinite - you get to keep it - but in effect whilst there'd be no sharp cut-off, the efforts the vendors make to give you access to your existing books in new formats - by making readers backwards-compatible, providing conversion services etc, would make N a finite but large number.
Which means for most people the deal is reasonable. Or can certainly be made reasonable at the right price.
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