Linux
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Give mint a try just to start. It's ubu-based, super polished and great for a first distro. That being said, don't think Linux doesn't have those update/dependency hell horror stories. If you go into it with realistic expectations, you'll have a great time with it.
Depends on distro, really.
Stick with a stable LTS branch of a well-established distro, and you're very unlikely to ever see issues after updating something.
Yeah, this is an issue I've yet to encounter using Mint for 2+ years now. It could happen, I've heard horror stories, but I've yet to actually experience it. Things just update and work, more or less. As a Windows refugee that wants things to just work, I adore Mint for this reason.