It fails completely for my use case, which is that every 6 months or so, I want to back up the 2000 or so pictures I've taken to a Samba share on a home server that I control. The closest equivalent would be iCloud, but I refuse to mortgage my family memories to vendor lock-in for a monthly fee.
You mentioned not wanting to mass-select 2000+ photos. If the photos you're uploading fall within a certain date range, you can open the Photos app, search for the date range of photos you want to upload (e.g. "April 20 2024 to today", or "sept 21 2018 to mar 2020"). It'll return photos taken in that date range, where you can tap 'See All', then 'Select' > 'Select All' at the top of the screen. Then you can hit the 'Share' dialogue and upload to your server through Files without having to scroll and select tons of individual pics. Keep in mind that you can't use a '-' in place of the word 'to' when specifying a date range for some reason.
If your images are family memories, you might be interested in Immich[1] (if you're open to making changes to your photo storage setup). Stand up and configure the local server, install the smartphone app, enable automatic sync, and it'll automatically upload new photos from your phone when you open the Immich app. No need for you to manually keep track of your photo syncs. Built to be a local Google Photos replacement. Has features like shared albums, face recognition/person naming, smart search, etc. AI tasks, like everything else, are done entirely locally. It's a nice piece of software, and lots of people (including privacy advocate Louis Rossmann) vouch for it.
As an alternative, here's a tiny script through iOS' Shortcuts app that selects photos in a date range and sends them to a Samba share through Files.[1] This time I actually tested, and was able to successfully run the Shortcut to copy a date range of photos/videos from the Photos app to my Samba share.
Quick instructions, in case you need them:
1. Create a new Shortcut and add a "Find Photos" module (You can search with the bar at the bottom). Add a filter, set it according to the screenshot[1], starting from "Date Taken" and ending at the stop date.
2. Add a "Save File" module beneath the Photos module (icon visible next to "Save Photos" in the screenshot). Shortcuts should auto-populate the selected photos as a variable so it reads "Save Photos". Hit the ">" next to "Save Photos" and tick any options you need.
3. Make sure to modify the date range each time you need to run the Shortcut.
You can also add/modify filters in each module to better suit your needs. For example, instead of "Date Taken" you could select by "Creation Date", or add in a "Media Type" filter so you only return photos and not videos (or vice-versa).
One thing to know: There's no progress bar so it's helpful to run the Shortcut from the Shortcuts app so you can see when it finishes executing/transferring. You should see a little 'stop' button with a semicircle around it when a Shortcut is executing from the app; it'll turn into a '...' button when it finishes.
A few things to note (applies to my above comment as well):
-If you have a less powerful iOS device, your screen may go semi-unresponsive during the upload process. My iPhone XS goes unresponsive until the upload finishes (less the ability to terminate the shortcut via the "stop" button), but my 2017 iPad Pro is totally usable during upload.
-You may get an error along the lines of "This Shortcut is trying to share more than [x] photos." You can allow this by going to iOS Settings > Shortcuts > Advanced, then toggling on "Allow Sharing Large Amounts of Data"
-Again, there's no progress bar, so it may help to run the Shortcut from the editing pane in the Shortcuts app. That way you can at least watch the app step through the script.
[1] https://www.icloud.com/shortcuts/d3258e1d720548cd9e635bbe090...
And it's fairly easy to select all 2,000 files -- in your camera roll, tap Select at top right, then just start dragging from the first photo. This lets you select a range rather than tapping them individually, and just keep dragging at the bottom and it will keep selecting while scrolling downwards. 2,000 photos might take a minute or two to select, but it's not that bad. Then just AirDrop.
Obviously you'll then need to move them from your Mac's internal drive to your desired SMB share.