First, if you know how to convert your ebooks with Calibre and sideload (like it seems you do), you're not locked to any ecosystem. You don't have to buy anything from Amazon if you don't want to. Also, you don't have to pay Amazon to remove the ads. You can buy an ad-free Kindle to begin with.
Second, you've not said where you live. Kindles support Overdrive in the US. If you live elsewhere and want Overdrive support, Kobo is better for you.
I have both the Oasis and the Libra and like both. If I could only afford one, I would be happy with either one of them (I don't use Overdrive). So, if you can live with 8GB instead of 32GB, I'd suggest to try the Libra. You can always return it, should you find it not to your liking, and wait for the Oasis sale.
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