I recently spent a good chunk of a day troubleshooting the problem "when certain people message my account on Apple Mail, I get the message twice."

Confirmed that it wasn't user error, and was common, never made got another inch of headway. My eventual diagnosis was "at least you're getting the message!"

Yeah I got my daughter a new Mac and synced it up to the iCloud so she could iMessage from the desktop and she got an odd (incomplete) set of contacts that don't seem to match any other device.

These are my main qualms with software these days: Logic went out of the window. Back in the days a good deal of software had great, albeit complex menus. The typical non-techy hated these interfaces because they didn't get results immediately and by not having an interest in technology most ruled out the idea of putting in some effort to learn the piece of software at hand. (no pain, no gain - duh!)

Next, companies "figured out" that usability is soo important and that it needs to get fixed because customers were having trouble. This was generally a wrong conclusion. Getting rid of complex menus doesn't necessarily increase usability. It irritates power users to no end and doesn't help casual users when they run into special cases. Heck, even the power users can't help the casual user anymore!

Every not completely trivial app(lication) should offer at least additionally a "complex" mode that offers a good old menu bar where deterministic, to some degree "atomic" functions (if you pardon the faulty analogy) are offered, grouped in a logically consistent way.