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Damn, you've definitely put in the work. Thank you for providing such a detailed feedback, meaning that thanks to you this is now the most up to date resource on how to move from Note Station to Joplin for future peeps that have your same problem!
I think you can rest assured that you've made the best choice in moving to a more flexible format now, regardless of any future "Joplin vs. Obsidian vs. whatever" discussions that might come up. Because if you're annoyed with Note Station now, I can absolutely guarantee that moving decades worth of .nsx notes for all your family, potentially manually, would have been hell on earth in the future.
One last experiment, now that you can: Let's say you wanna move from Joplin to Obsidian tomorrow. These are the #1 and #2 results when searching for "Import Joplin to Obsidian". Just take a look. It's almost comically easy compared to now, so I'd say bright times are ahead :)
Thanks for the feedback. I finally got all my files over. I got past the 250mg limit by going into the user admin on the server and changing the default to 1tb(the max). The devs says that it's a limitation of postgre but it seems to be working.
A simple way to find all my missing files was to search in Joplin for"NOT FOUND" and all the notes with missing files show up. Just went one by one reuploading the files.
One of the highlights of Notestation is that it's designed for normies. It uses Rich text editor.
My first client(my wife) on Joplin is already complaining because the android client is markdowns only. She is semi ok with it because the desktop client is a fake Rich text editor wrapper.
Obsidian is 100% markdowns. Not going to fly with the rest of the family.
Thanks again for the help!!