Everything iCloud is even worse overall when you have an older OS or two in the mix. My iPad and iPhone are up-to-date, but not my Macs.
Yesterday I got a reply to a conversation with mixed iMessage and SMS messages. The new message showed in a notification, and in the preview of the conversation in Messages (the Mac app), but not in the actual chat interface itself in Messages. Then there’s the need to clean my messages of attachments… separately on each device, despite Messages in the Cloud being enabled everywhere. Technically they all support this, but, technically, it doesn’t actually work. This is becoming the “norm” with my Apple experience.
High Sierra gets less usable with the ecosystem and availability of software monthly. I’ve been trying to hold on to my computer purchase stash until Apple shows some clear sign that I’m not going to get anything better than the Mac Studio, in my conceivable price range. I can buy a new machine once, for the next … 8-10 years? Longer? Makes it hard to actually commit to updating, as I don’t want to regret the purchase soon after.
But damn, it’s getting almost impossible to deal with all the stuff that’s broken (iCloud, webpages), software I have that cannot be updated, or new software I can’t try because I’m stuck on High Sierra on my obsolete machines.