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You having regrets depends on your expectations. If you want a very stable system with little maintenance then you’ll be happy. Packages will be older but that’s what makes it easy to keep stable.
I’m not personally a fan of vanilla Debian because the stable versions are a bit too outdated for the things I like to work with. I do use Debian derivatives though the LTS versions.
I don’t find this surprising at all. So many windows updates broke dual booting over years. They really don’t care and have no need to.