One of the craziest ones are basic search in osx has been broken for 10 years now - it might work for a while but for power users it almost always gets weird then stops working.

Another wild one is syncing photos between iphone and mac meant ‘this photo will sync at random point in the next 5 days’ - it’s just recently been fixed after like 8 years of not working.

And don’t even try to use their stupidly simple proprietary apps like Numbers where basic spreadsheet functionality is bizarre or missing.

Mac is still my favourite but i don’t get why a trillion dollar company can’t fix their software for what’s ‘pennies’ for them.