Steve, I feel your pain and have been through almost the exact same issues - getting photos from phone to computer, transferring data between old and new tablets, etc.  It's amazing all the different cords there are. :ermm:

The latest "interesting" hardware issue I've run into is with SD card readers.  I put trail cameras up in the woods and I wanted a quick way to be able to view the images off the cards right on my phone while in the woods.  I bought one and it just plain didn't work - Nothing. (In order to get a refund, I had to upload a video showing it didn't work - and they wanted it under 5MB - that was a challenge!)  On a second one, I had the USB-C plug break off in my phone.  And what I've noticed about both of the ones that I've gotten to work is that my phone instantly writes TO them instead of reading FROM them.  I get some "default phone path" directories on the SD cards.  (What I don't know is if it's ever over-written the pictures that my cameras have taken?!?!?)  To protect myself now, I always "lock" the SD cards before I insert them. 😉