If I had to choose one I'd use Obsidian because Bear's features are a subset of what Obsidian does, but Bear is still nice.
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Minimal tags-first organization, rather than Obsidians poorly thought out mix of files and tags.
...and that's it. It's the only app that has never given me any reason to switch in ~10 years.
I pay for Bear because it’s a native app and not in the weird uncanny valley of Electron apps that almost feel native until you hit the rough edges. It syncs with iCloud. It supports Shortcuts. It’s as responsive to keystrokes and keyboard shortcuts as any other Mac app. Basically, it just feels good to me and I enjoy using it.
Obsidian’s awesome. It’s also an ADHD tarpit for me. I can way too easily get distracted into optimizing my workflow instead of, you know, just typing notes into it. That’s a me problem, not a them problem. I don’t mean it as a criticism against Obsidian. It’s just not the right tool for me.