To make it work (if it worked), one needs to uncheck $ReadOnly in the watched note.
BTW, changes made in Tinderbox to DEVONthink watched documents do not get synced back to DEVONthink, either. (When $ReadOnly <> true)
I’m with you on 1 - I’ve used Tinderbox for many years now but have certainly only ever scratched the surface. However, I use it every day and it’s indispensable for an open-ended history of medicine project which has whole warrens of detours, all of which are kept in easy contact with the main thread and each other in just a few Tinderbox docs. (+ DT3 (holding) + Scrivener (prose) + Drafts (iPhone moments))
I tried Obsidian for a while (and a few others) but - and this might sound a tad odd - Tinderbox is the only software of this kind in which I have never felt claustrophobic or overwhelmed by the mass of material I am working with.
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Hey there, not at all. Tinderbox is extremely useful right out of the gate. It unfolds like a glorious onion with endless layers, not just internally, but it also connects with other apps/experiences and standards. It is extremely extensible. Also, everything I learned I picked up from the community. Ask us anything, and we’ll help you out. 
On that now, what type of work are you looking to get done? I’m hosting a workshop next Friday morning, maybe you’d like to join us.
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Hmm…this is a hard question. It is comparing apples and oranges. Both apps have their place, and I know many people that use both. Personally, as I am focused on not just taking notes to produce publishable output, going down that Tinderbox path is a no-brainer. Tinderbox’s core capabilities (prototypes, attributes, an action code, and export code/templates) have no parallel in any other app I’ve seen. I’ve tried using Obsidian several times and get running into deadends. With Tinderbox I can curate my knowledge and assemble/reassemble it into any output that I want. It can be easy to fall into the trap of this app doing it this way, so I want that app to do it that way, too. Tinderbox is extremely flexible; it just takes some getting used to. Schedule a call with me via DM, and I’ll give you a private demo.
Honestly, and I’m not being melodramatic as the community can attest to my evaluation, Tinderbox, and this community fundamentally and positively affect me and my life. It has helped me see and contribute to the world in new ways.
I don’t think so. I have several TBX files/projects with over 10,000 notes, all linked together. I tend to work in one and then split them off once they start to specialize. By the time you get to this point, however, I’m confident that you’l have all the skills you’ll need to thrive with the tool.