Organizing photos in an iPad Pro v a MacBook Air

You need a Mac. I, too, have been scanning family pictures and organizing them, and Photos on the Mac has several tools that make it all much easier. iOS only shows captions for pictures, but the Mac allows you to use keywords and titles. And Photos on the Mac has Smart Albums. So you can make a Smart Album that grabs all the pictures with with criteria like "keyword=Zoo AND person= Bertha," for instance. You can easily make keywords to keep pictures in separate albums. While the Smart Albums don't show in iOS, you can copy the pictures from one into a regular album so it will sync through iCloud with your phone and iPad. Some batch operations are difficult, but there are several 3rd party apps that help a lot.

On a Mac, also, you can have several separate Libraries. So I have a Library of my wife's old family pictures and a Library of my own old family pictures. I have another Library of only Favorites that a I've copied from other Libraries, and that is the one I connect to iCloud so I can see and show those pictures with my iPad or my iPhone.

I'm pretty happy with Photos for being able to find the pictures I want to look at or show to others.

It's always a bit weird to change platforms. Windows and Macs have gotten closer, but I've felt the same way about using PCs--it's all the little things and muscle memory that makes your fingers go one way when they should go the other. You can, of course, run Windows on a Mac. (But, he asks, why would you?) Also, you can get questions answered here.

There are three highly trusted apps that I and many others use. One I've used for, I swear, thirty-some-odd years, is GraphicConverter ($40). This excels at doing batch operations like changing file names or changing metadata. But GraphicConverter works outside of Photos. It won't (and shouldn't -- hence the bold italics) work inside the Photos Library. So I use it to alter files before I import them to Photos. For instance, I use a digital camera that records the focal length of the lens. But some of my old manual lenses don't transmit that info, so 0mm is recorded. I can use GraphicConverter to put the pictures in order of focal length, and then change the metadata of just the ones with 0s. This could have been really hard, but GC makes it work.I also use GC to crop and change image resolutions of screenshots that I upload to this site. And lots more.

PowerPhotos ($30) has been a trusted app since the early days of iPhoto, like 2003. PowerPhotos does batch operations actually using Photos, so there is no danger of corrupting the Photos database. It can help look for duplicates, swap pictures between libraries, merge libraries, and so on.

I use Photos Workbench ($30) mostly to batch modify titles for pictures. This is a newer app from a trusted software company.

None of these is subscription based-- they don't connect to the internet, and their support is superb.

I currently have all my jpeg images in iCloud, including the purely functional jpegs I discussed before. Is this a mistake even with a Mac?

You can put everything in iCloud, but then every thing shows up on your phone, even if you don't want it there. So I wouldn't. I have a separate Library for work things.

You don't have to have separate libraries to keep things separate--folders in Photos can keep things apart. But I found that work stuff just got in the way when I was organizing personal pictures. And I found that I kept getting confused about who was exactly who and belonged to whom when I had old family pictures from my wife and me together in the same Library. I could just be me.