Finally made the jump after putting it off for years. Export came out as one giant file, half my attachments were dead links, and internal note links pointed nowhere. Took a weekend to untangle everything by hand.
The pattern that came out of it, if it’s useful to anyone else planning the same move: plain text and formatting survive fine, images mostly survive, but file attachments, internal links, tags, checklist states, and note history are all genuinely at risk depending on the export path.
Since then I’ve been running the same export/import check for a few other people before they commit, mostly out of curiosity how consistent the breakage actually is across different setups (Evernote/Notion/Apple Notes/Roam to Obsidian). If anyone here is on the fence about migrating and wants to know what they’d actually lose before deleting the original, happy to run your case too, free - reply here or DM me and I’ll send the link over (new account here, forum won’t let me post links yet).
Curious if others who’ve made this move hit the same set of breakages, or if it varies more than I’d expect.
I want to add one thing from my own experience with data migrations. The bugs that really hurt are not the ones you can see. You can easily spot dead links and fix them over a weekend. The real problem is a file that looks perfect but is actually broken.
I once had a file that opened and displayed completely fine. But every other tool treated it as a binary file because it had some hidden NUL bytes inside. I got no warnings. It just quietly stopped working with my system, and I only noticed it months later.
Because of this, I highly recommend comparing exact counts before and after you migrate:
Total number of notes
Total number of attachments on your disk
Total number of internal links
If you start with 4,000 notes and get 3,980 out, you need to know this on day one. You do not want to discover it eight months later when you need that one missing file.
You also mentioned checklists. Do not just open a few random notes to verify them. Search your raw markdown for - [ ] and - [x] and compare the total numbers before and after. This often fails silently in a very annoying way. All your checkboxes might still be there, but they all become unchecked. Everything looks completely normal until you open an old project and cannot tell what you already finished.
Testing your export before fully committing is the best approach. Surprisingly few people do this, and most only realize it when it is already too late.