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I've just gone through a similar analysis and can offer a few comments. All of your options are top choices so the final pick may involve some hair splitting unless one particular feature really seals it for you.
On YouTube videos comparing the Libra and Oasis side by side, the Libras that I saw had kind of a blue/green hue to the screen compared to the Oasis. I also came across some comments of Libra screen lighting being non-uniform, and I never saw that complaint about the Oasis. So I decided that I preferred the Oasis screen.
I've put library books on my old Kindle for years, both via email and side loading, with no problem and from what I can tell Kobo is equally easy.
I came across a complaint or two about Kobo service/support. Amazon customer service in my experience has been top notch and I never read a complaint about it re the Oasis.
For years Amazon has offered a trade-in policy that allows easy and relatively economical upgrade path. I don't know if Kobo does but it could be something to check. Amazon also regularly puts their e-readers on sale at least twice a year.
The biggest gripe I saw about the Oasis was regarding battery life. The curious thing was the inconsistency. Some people claim very short battery life while others claim weeks or months of battery life. Hard to tell for sure, but I decided that this might be due to some people leaving backlight turned all the way up all the time, WiFi on all the time, etc. while others did not. Apparently the Oasis also tries to perform an auto-indexing function in the background which burns battery if you do not stop the indexing.
Anyway, I decided to try the Oasis and with Black Friday pricing and trade in I got it for $115 which for me clearly gave it the advantage over the Libra.
Good luck with your decision!
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