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I've been using Bear for a long time. I tried Obsidian to move off Bear, but it didn't last long. The Bear UX is just great and that's what's kept me around this long.
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I use both Bear and Obsidian. I do some long-form writing in Bear but keep all of my structured notes and markdown in Obsidian. Obsidian has much better tooling and many more features, but Bear has a very pleasant experience for writing. It's very simple but if it's all you need it's very polished.

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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Easily the best Markdown editor. I hate all rich-text editors except Bear.

Images appear as thumbnails in the notes-list.

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.

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Obsidian is a closed source Obsidian.

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.

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Obsidian is not open source.
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