Long time Org-moder, 1-year Obsidian user here.

I love org-mode with all my heart. I used it to run a consulting company for a decade and organize my entire life (reminder to mail my mom a birthday card? Recurring org task. Task breakdown and schedule for clients? Org.) I used it to keep all of my implementation and debugging notes. I’ve used it like Jupyter notebooks with inline code blocks. I’ve written tons of LaTeX math in it.

For what I use it for, Org has a ton of magic sauce that Obsidian doesn’t have for me. But Obsidian has one feature that, sadly, dominates all of that magic: ease of use on iDevices, including offline use.

I can sit and work on Obsidian documents on my iPad+keyboard on an airplane without Internet access. I can reference my documents and update my todo lists from my iPhone without needing to SSH somewhere. The sync service is super smooth and the (much smaller) set of features is enough for most of my daily use.

I miss org-mode very much though and if I were to change jobs and spend less time work-travelling I would probably switch back to it.

One of the biggest reasons that I was comfortable using Obsidian specifically is because the disk format is mostly just Markdown (mod the infinite canvas stuff, which is documented JSON). Being locally-stored Markdown instead of a proprietary format, I feel like there’s a reasonable pathway for me to reimport all of my notes back into Org-mode in the future if I decide to go that way (eg Pandoc)

Obsidian is a great app and probably the closest thing spiritually to org-mode for those who aren't interested in emacs, but Obsidian doesn't (currently) come close to the whole package.

Just as some examples: outline-centric without plugins (this allows functions like narrowing/hoisting to a particular part of the outline that you can't do in Obsidian), substantially better export/document authoring, org-babel (think Jupyter style notebooks or literate programming) integrated into the core concept, functionality integrated into the core system rather than siloed into plugins (org-agenda is essentially a combo of the dataview plugin and the todo plugin in Obsidian, but built to work together, and completely integrated with things like timekeeping/clocking for those who bill hourly, which is still missing from Obsidian). Plus some of the keyboard-centric stuff in org-mode is just really nice, down to little niceties like how you can manipulate dates and times without clicking around. Then there's all the benefits of emacs on top of that.

To some extent a lot of this derives from org's 22 year history. It's a very mature system, with loads of functionality.

One strength of Obsidian though is canvas mode. There aren't great emacs solutions like that at the moment.

I use both, while Obsidian is good and has lot in common but for some reason org-mode still feels more useful and permanent. If it something important for me personally I most likely will put it in 'org' but if I just need write something of temporary nature like documentation peace for work I might prefer Obsidian for that. Also org-mode TODOs/agenda stuff very helpful for triage of tasks and prioritization (I think it's just habit that has some 'migration' cost so I not really considering it as big benefit over other tools)

Never tried it. What I have "just works" for me. Also I value having everything local-first in plaintext.

The ability to get on with life with the absence of global organisation is my saviour. While any given org file may be well structured, my org files directory is a disaster zone.

I just use rgrep and text search to get around. It's great!