After much wringing of hands and a near disaster, I am back to using Lightroom Classic as the core of my workflow. The goal is to have a stable local set of files, but also benefit from cloud sync and editing.
I started by cleaning up and reimporting everything into Classic and deleting the entire Lightroom CC library. I then created a brand new Classic catalog and imported a combination of old catalogs and folders of images. One side effect of this is that I now have a lot of duplicate images because I imported everything, including the "./Processed" folders which normally aren't added to the catalog. I'll have to live with this.
All new photos will be imported into Classic on my iMac (home). If there are a lot of images to be imported, I'll first import them into Photo Mechanic and add keywords and captions before then importing into the Lightroom catalog.
The current year's photos are stored on the local hard drive. Prior years are moved (using Lightroom) to the Synology at /home/Photos/YYYY
In Lightroom's preferences, I've enabled "Specify location for Lightroom CC ecosystem's images", set to
/Users/jbaty/Pictures/Photos. I also enabled subfolders by date and set it as
YYYY/MM. This meant changing my long-standing format of
03-March 2018 for monthly folders but the upside is that anything I happen to import into Lightroom CC on mobile (or that are automatically added from Apple Photos) ends up in the same place as my local imports, e.g.
/Users/jbaty/Pictures/Photos/2019/03/ Again, I can live with that.
For any photos originating in Classic that I would like to have also synced to CC, I add to synced collections.
What I hope this all means is that I have all my photos safely stored on my local system in a place I dictate, and with file names I control. In addition, new iPhone photos are automatically brought in via Lightroom CC and stored locally with everything else. If I'm traveling, I can choose to import into CC on my iPad Pro and do some editing there, knowing it'll all sync back into Classic later. Also, it's nice that file names edited locally are synced with the CC versions. This makes me feel better.