Martin - along with pretty much everyone else I know and have exposed to my strange backup and file syncing habits - pointed out that growing up and paying for even a bit of Icloud storage would neatly solve so many of the problems I have created for myself.
The first thing I thought of at the moment was to get rid of my reliance on that free Dropbox acount and whatever hiccups Maestral are having at the moment. I started wondering if Icloud would be as flexible of a file storage as Dropbox has been, but after doing just a minimal bit of research I realized that would not be a problem at all. The thing is, the main thing I want flexible file storage for is accessing my notes, which I do using Obsidian on my computers and 1writer on my Ios devices. But if I get myself together and move to Icloud, I can simply set up my vault on Icloud drive and start using Obsidian on Ios as well. So my day to day convenience would actually increase markedly.
One open question is whether keeping my website on Icloud drive would work as well as it has in Dropbox. I have simply dumped the whole thing there, both the raw text files and the generated output, and I suspect that is not a brilliant idea to delete and recreate hundreds of little files on each rebuild. But my generator script already has a argument for output folder, so I could easily pull it apart and store the built files locally. It just has never happened because Dropbox has been too good about handling the situation.
Then, there were the massive side (from this point of view) benefits. If I go for the serious storage options, I will also completely solve photo storage and backup for the whole family. No more kids Ipads running out of space. No more me sitting down at one assigned computer to look at - and import - my photos. The Icloud photo library will solve all that for us. (I will of course still have that computer download all the photos and back them up to Backblaze, I am not a crazy person.)
I briefly looked at the prices for Apple one - Apple's all in one subscription offering - but since I do not actually want any of the other services it did not feel like a good deal.
We will see what happens. Giving Icloud a real shot certainly seems like it could be worth spending some holiday time on.