Iāve found some info on CloudKit which, for me, was a total waste of time. Reading the following was like eavesdropping on Klingons.
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That line is hilarious! 
I have no idea when or where, but Iām absolutely stealing it and using it.
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I had my own issues with Ulysses sync a few years back. Sounds as if youāve been down all the appropriate rabbitholes on the subject, but Iāll toss in one more just in case it might help you or others in the struggle:
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We can all see youāve been through a lot @Bmosbacker;
Hereās an emotional support puppy for you
( just a random cute photo from the internet, but it looks like itās imminently ready for some fun havoc!)
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Maybe it will help you decide to see where things are in a few years ahead. Scrivener, I believe, will be replaced by a more modern, lightweight app that likely will become Ā«the new oneĀ». So you are kind of betting on a dead horse here.
Yes, that has concerned me as well. But, given that I canāt trust Ulysses, Scrivener seems to be my only viable option for writing a large non-fiction book. That said, Iām open to suggestions. I have two major complaints with Scrivener: 1) the mobile app leaves a lot to be desired and 2) compiling is a complex process, overly complex in my estimation.
EveryoneāIād love to hear of a better solution for a book project. I have good options for other writing, but a rather complex non-fiction book is another matter.
Then, do not rely on it for other than writing and editing. I works fine for that. Focus on the bigger picture for your big project.
@rms and others. I have a crazy idea.
I think I can eliminate nearly all of my writing frustrations by exporting my book project from Scrivener to Markdown. From there, Iāll write each remaining chapter in iA Writer. Once the first draft is complete, I can use iA Writerās Transclusion feature to combine all the chapters and export the full manuscript to Word for final editing. Hereās why this may make sense:
- I already own iA Writer on all my devices.
- Itās a native app thatās regularly updated.
- Thereās no subscription.
- Syncing is lightning-fast and has never failed me.
- I can write quickly in Markdown and know how to format footnotes properlyānot inline.
- I can use Preview with scrolling disabled to view an outline of longer chaptersāsomething I admittedly tend to over-structure.
Obsidian is another option, but I donāt like Electron-based apps, and many of its plug-ins donāt work well on mobile.
Frankly, Iām tired of dealing with the constant friction. Maybe the problem is meābut the frustration is real.
So, am I crazy? If so, tell me now. I wonāt be surprised or offended! 
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Definitely not, but it sounds like you have reached the āfish or cut baitā phase of your project.
As for step 4. IMO, syncing and investing have something in common. āPast performance is no guarantee of future resultsā
As for step 4. IMO, syncing and investing have something in common. āPast performance is no guarantee of future resultsā
Can you elaborate?
I meant just because something has worked well in the past, doesnāt mean it will continue.
Iām not a heavy iCloud user. But since I run Advanced Data Protection, I keep copies of some sensitive (medical, etc) files on iCloud in case I or my family should need them. They donāt always sync right away, and even though I have them marked ākeep downloadedā, a few never do.
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@Bmosbacker I think you really need a version control system in your work flow. The sync issues you have can be eliminated by adding this to your workflow.
- Get yourself a private GitHub repository.
- Upload your contents at the end of each day or each week or even at critical points. It can be even every hour or as and when you please.
- you can still continue to write in Obsidian or Ulysses or IA Writer. Just save the material or export as markdown files.
- check in into GitHub
- when you have sync issues you can just download the saved intact copy anytime to any device.
You can spend some time on researching this workflow and I believe that it will fix your issues.
Happy writing.
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Mellel is an excellent option which I do not see in your list of previously trialed apps. It is a word processor, ie you would be working with formatted text, not markdown. It has a robust styles system, citations system (especially when paired with Bookends), and a great outliner. I prefer it to Scrivener for long-form writing: it is more linear, less segmented, which I find helps me produce a better final product. A new version planned will introduce āconditional sectionsā to the outline which should allow more Scrivener-like flexibility (that still avoids the ācompileā step). Mellel has an iPad app which I have not used but seems to have been well-received. The developer asked his users if they wanted an iPhone version and the consensus on the forum seemed to be ānoā. If that doesnāt matter to you, then I suggest you check out Mellel if you havenāt already!
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Your not crazy at all. Markdown is the standard for devs and i am confident it will be the standard for all documents in next 3 years. The nightmare of converting pdfs for AI uploads made alot of people think about file formats for documents. Cant wait to cancel my Adobe subscriptions 
I am literally in the process of moving all of the applications i have used over the years (drafts, notion, sharepoint, google drive) to a simple file system on icloud (model context protocol features MCP on claude desktop will probably save me 6 to 8 months of work).
Folders are based on file types and I am using markdown for everything that is considered a document.
Look into what these MCP servers can doā¦it is worth your time.
I started using Neovim after months of learning vim motions and this is the way for me.
Telescope on Neovim blew my mind.
I was going to suggest Mellel. Rock solid app.
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Iām getting to the point where I, as a software user, am not interested in spending extended periods of time on troubleshooting hard-to-pin-down major issues.
To be clear, I try to be as helpful as I can the majority of the time. If I can document a problem, Iāll happily file a bug report. Iāve reported numerous bugs to devs, and when they asked for specifics Iāve given them screencasts to show them what was going on. Many of those bugs have been fixed.
But if an app loses data at unpredictable times for unknown reasons, I have zero interest in continuing to use it in order to help the dev troubleshoot.
A way to recover from data loss is important, but @Bmosbacker already has that. What needs to happen is for the data loss to stop occurring, which recovery procedures donāt address. Or put differently, āa fire extinguisher is important - but the goal is to not to have the fire in the first place.ā
On the off chance you need an additional emotional support puppy, our dog is happy to offer her services as well. 
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I am not convinced whether you are searching for a better tool for writing or a better tool for managing the content that goes into the document that you want to write or a better tool for publishing the document once it has all its content. On top of this, I am not convinced that you have yet agreed that you must not operate on the principle that both the macOS and the iPadOS must always provide you with exactly the same experience to complete any one of the three aims, let alone will do all three aims with the same tool or tool sets with the same degree of fidelity.
writing: Ulysses on macOS
editing (ONLY!): PDF Expert on iPadOS
content management: Finder on macOS, TimeMachine to external SSD
research: ??? on iPadOS or macOS
outlining: ??? on macOS
Done!
ā
JJW
Markdown is not even its own standard now, let alone that it should be a standard later, let alone that it is not a standard that is robust enough to generate precisely-defined page formats, let alone that it cannot even begin to manage ADA compliance standards, let alone ā¦
In summary, I expect this confidence should have a bit narrower scope than āā¦ for all documentsā and perhaps also a bit longer time frame than āā¦ next 3 yearsā.
ā
JJW
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totally fair points, and I appreciate the thoughtful pushback!
Youāre right that Markdown isnāt built to be the end-all for every type of document, especially when it comes to print formatting, accessibility standards, or exact layout control.
My excitement is more about the simplicity and flexibility it brings for certain types of content ā notes, ideas, light docs, or any writing that benefits from being portable, version-controlled, and future-proof.
I probably got carried away in the optimism 
ā I donāt actually think Markdown will replace PDFs or Word across the board, especially in regulated or design-heavy domains. But for individuals or small teams managing knowledge in a more fluid, interoperable way, itās been a breath of fresh air.
Appreciate the grounding reminder ā scope and context really do matter when talking about āstandardsā