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Paste from markdown (Chrome only) works _really_ well for me. What are the extra steps you’re running into?
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Interesting, in my Arc browser, I just tried File -> open -> upload -> blah.md and it does seem to render fine. This exact thing did not work a few weeks ago, meaning the various header markers etc showed up as raw "##" etc, and I had to further select something like "open as new doc" to finally make it look good.
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Right click > "Paste from Markdown" instead of just straight up pasting in
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Images wouldn't work though, right? I'd be amazed if that worked. My CLI tools handle those.
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Obsidian has become almost an operating system for working with markdown. Its Live View / Edit mode is excellent (WYSIWYG) and its ability to accept pasted content and handle it appropriately is good and getting better. Its plugin/extension ecosystem is robust (and has a low barrier to entry), and now that it has a CLI I expect to see an acceleration of clever workflows and integrations.

No affiliation, just a very happy ~early adopter and daily user.

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BUT the main supported sync module is cloud only they wont let you self host for free which is really shitty and lame.
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Wow, that's a strong opinion and harsh words that come across as really entitled, and probably unfair. From my PoV, they're a tiny, scrappy, transparent and likeable company who built and maintain a fantastic software application that radically improved ~everything about my daily workflow and PKM. I get more value out of Obsidian in a day than most other apps in their entire lifespan. The core app is free! They have to eat. I'd probably throw $ at them even if they didn't charge a few bucks / month for Sync. (Which works flawlessly.) Sure it'd be cool if you could self-host their Sync module -- but many Obsidian users use other DIY approaches for sync; in the end it's markdown files on a local disk, do with it what you will.
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git + cron
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I’m intrigued by their recent CLI release as well. I’ll have to check out the markdown edit support too, thanks
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interesting we have a very similar internal flow - we like working in markdown but our customers want to leave feedback in Google docs, so we also have an md -> gdoc tool. We don't do the reverse as we ask them to only leave comments/suggested changes and we apply those directly to the markdown and re-export.

I ran into similar issues as you for the image handling, and the work around I use is to use pandoc to convert to docx as a first step and then import that as a Google Doc using the API, as Google Docs seems to handle docx much better than markdown from what I've seen.

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