I Love my Mac, but...

Oh gosh! What a pain with those random file names. That would drive me crazy! I sure hope you're able to figure out a better solution with Lightroom that works for you.

I am just taking a folder at a time and clearing out the bad photos and renaming the day. Then over time I'll rename the actual photos. It's too hard to have them NOT be in numerical order, but I can deal with a wonky file code if I know the approximate date. I'm also using the cloud backup which I never did before. I don't like the cloud and I can't really say why. It just feels wrong. LOL
 
I am just taking a folder at a time and clearing out the bad photos and renaming the day. Then over time I'll rename the actual photos. It's too hard to have them NOT be in numerical order, but I can deal with a wonky file code if I know the approximate date. I'm also using the cloud backup which I never did before. I don't like the cloud and I can't really say why. It just feels wrong. LOL

That sounds like a good plan to make it manageable moving forward. I totally get what you're saying about the cloud. I don't love it either and I never rely on it as my only backup, but it has come in handy a couple of times, so there is that. :giggle
 
I guess another option for getting your current photos transferred would be to use air drop if you have an iPhone.
 
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