Was recently in a similar predicament with 12 year old Mac mini and 13 year old MacBook Pro. Abandoned the MacBook, gave the mini to a grandson, and got a Mac Studio designed to my specifications. My ancient thunderbolt monitor works well with an adapter. I now use an ipad for photo work when traveling, it is smaller/lighter and adequate for my purposes since I don't do final editing till I get home and get everything backed up and on the big monitor.

I use my IPad Pro (it's an old one but still works great) when traveling. Like at least one other described, I download daily into Lightroom Mobile from camera card using the dongle device. The mobile ap is usually all I need on the road, but I have Photoshop mobile and various plugins if I have some downtime to allow more editing. When I get home I can either move the edited photos from Adobe cloud or simply download straight from the camera cards to my desktop where I do more serious editing on the big screen with all my tools available. Eventually I delete them from the ipad to make room for more, as I seldom need them there after I get them into my primary desktop system. The IPad is a temporary holding/working system. I did the same when I used a laptop for travel.

With a keyboard case, I get similar performance to a laptop with a lighter, smaller device that I can stuff into my camera bag or even my purse. I use an Apple Pencil for more precise editing.

You do have to spend a bit of time sorting out how you want to make the ipad work with Adobe cloud, and with the built in Apple programs.

I only recently upgraded to Ventura, and will take my time going to Sonoma. I never jump on a new OS upgrade right away. As others have said, new OS versions often take a few updates to get the kinks out. It sounds like your computer has a quirky relationship with Apple Mail. I've had that on my MacBook Pro before too.

If you have yet not tried removing the accounts and adding them back, that is easy and worth a try. Otherwise, I'd encourage you to keep on pestering Apple Support till you get a resolution. And if you haven't done so yet, I'd post on the Apple forum boards specific to the email problem.

Time Machine WILL back up your external drive(s) if you tell it to. I have used Time Machine to back up both my mac and my two photo drives onto a large LaCie external for years. When one photo drive failed last year I used TM to restore my photos to a new drive quickly and easily.

My secondary backup is to Backblaze, which backs up my main computer and the two external photo drives to the cloud. The first Backblaze backup took a while, but after that it's been quick and easy.

Yes. There is a little program called Creative Cloud Desktop that you'll be prompted to install. It gives you easy access to install any or all the programs you are entitled to, and updates as they are released (you'll be surprised how often new versions are offered, and how many new toys you get with a subscription), plus a lot of other information, plus any free beta programs you might want to try, and past versions if you ever find that a new upgrade doesn't play well with your other programs.

If you're still at version 5, your new Lightroom will keep you entertained a good while. The masking features alone are worth the investment.

The photography plan is what most of us use. It includes LR Classic (the one that lives on your computer, along with the photos you download to your computer/drives). It also includes the cloud based Lightroom (which most of us do not use), Photoshop (which many of us use as an adjunct to LR Classic), Bridge, ACR, and mobile versions of Photoshop and LR in case you want them on your phone or ipad. It also has some cloud storage but certainly not enough to handle your whole photo catalog. It is a fantastic bargain for $10 a month. You don't have to install all the goodies, but be open to eventually learning what they do and how they can help you.

The M series Apple computers are great for photography. I have no trouble running any of the Adobe programs but because I have a handful of very old plugins whose companies did not update them in recent history, I run the Adobe host programs via Rosetta. Rosetta lets me use plugins that are ridiculously outdated as well as the new ones that have been adjusted for the M series. I was worried Rosetta would slow things down but if it did, it was by milliseconds. Printers and other peripherals may require new drivers that you can get only from the companies who made them. Some peripherals may require adaptive plugs (my 14 year old monitor did) My old external drives required reformatting. The generic Apple print system is pretty basic and would not be adaptable enough for my use. Epson has specific drivers for the M macs that offer all the settings you may need, but I don't use Canon so don't know. My Wacom tablet has only recently sorted out their new drivers but have them working now. Making a switch to a new computer or new system software often has its headaches but it is worth working through the kinks to enjoy the benefits.

In addition to explaining the steps you're trying, if you include a screenshot showing the "access denied" message you're getting when you try to post the avatar, that might help others help you more. New Apple machines/systems have a lot more "protections" involving permissions settings. With my new Studio, I've had to tinker with permissions more than I ever have before. It's seems extra particular about things that are stored on external disks and that's where all my photos live. I had it all sorted, but had to redo some of it when I installed new versions of LR/PS.

I am so sorry to hear that, Bob was a source of inspiration to me and taught me a lot about editing monochrome images. I called him the CloudMaster because of his skill in capturing/rendering beautiful clouds. Once I received a surprise package from Arizona, and was thrilled to find it held a beautiful print of one of his landscapes I had admired, with those fabulous clouds. It hangs in my living room.

Our online friends as just as "real" as the ones who live nearby, and they can bless our lives in special, lasting ways.

Videos by Kost, and info on Lightroom Queen website, can be very helpful to you.

I have all my photos on an external drive, in a folder structure by year/month/date. I create the new folders within this structure manually, import new photos into them manually and bring them into LRClassic using the "add photos" command. I have tried the automated method and I prefer my own. I like to control the process myself, that way I'm sure everything ends up where I want it. I add some keywords as I import, and refine them later. I use collections as a flexible tool to gather up images I need for some purpose (like making a calendar or preparing for a exhibit) but collections don't change where anything goes nor do they duplicate anything.

Agree this info may help people help you better. Also:
Have you recently updated your Mac OS?
Did you install anything new or modify anything between the time it last worked and the time it quit working?
Have you tried having Lightroom import directly from the card? Did that work?


Some other ideas:
Put a new card in the camera and take a new sequence of photos, and try to import them. Any difference?
Watch the attempted import on the console. Any clues?
While you're in the console look through the various reports. Any clues?
Have you run system diagnostics? On both your hard drive and any externals? Any clues?

Some suggestions:
Post your problem on the Lightroom Queen site and the Apple support site.

I have used Lightroom and PS for 15 years and only once have I had a totally confounding problem that Adobe tech could not solve. The good folks on LQ and Apple forums helped me find/resolve the problem.

Once you convert them to jpegs, why not just upload them yourself to her shutterfly album and eliminate the problem of sending them to her? She can create a shared album, send you a link and you can add them directly.

https://support.shutterfly.com/s/article/share-my-photos#sharing-albums

If she uses shutterfly albums regularly, this might be a skill you'll use again in the future.

The old site is still working, too. You might have to clear your cache, remove cookies, or other maneuvers to get your browser to load it, but it's there. They seem to have a skeleton staff, and a lot of users have moved to one of two spinoffs. (I moved to the one Linda mentioned, DPRev) Some users have made it a point to stay at the old site till the lights go out or till someone announces a new owner/direction. Activity is reduced but it's not dead yet. No one knows whether the site will be open long term and if so, what it will be doing.

To answer your question briefly, no you are not too old to learn LR/PS or whatever else you decide you want to learn. The real question is, do you want to learn it? I'm 75 and becoming more proficient with both programs and many external plugins all the time. It is a bit unsettling when you first transition from jpeg to raw, for some reason, but you could always shoot both till you reach a comfort level. Don't worry about trying to learn everything before your trip, but consider capturing your trip in both formats and using those photos as your entry into the world of LR/PS when you get home. It is annoying to fuss with new technology while traveling. The $10 a month program is way more than $10 worth of fun every month. I'd pay more, but don't tell Adobe.

That should work. But...Did you try the Save To Files option? Once you choose that option, you still will not see Google Drive unless you activate it in the submenu. In iOS that submenu is represented by 3 dots, indicating there's stuff hiding there. I can't imagine why it would be different on Android but perhaps it is.