I think Apple are failing to realise that their professional creative market was actually what drove their 'cool' for years. They've been undermining and frankly pissing off professional users - i.e. trend setting designers, digital artists, photographers, journalists, video producers, web developers etc etc for some years now by mucking around with dropping support for products.
1. Final Cut Pro had become an industry standard almost and it was radically changed causing major upheaval for video editors and producers who had trusted it.
2. Aperture was dropped.
3. They made the MacPro into some kind of weird looking ornament instead of the ultra-practical workhorse that many pro-users loved. Did they actually ask pro-users what they wanted? Nope! They decided that the one thing that your typical music producer or graphic designer would want is a tiny computer that you can't expand easily without a spaghetti junction of wires.
4. Then to top it off they produce a professional-oriented laptop (certainly price wise anyway) that has removed all the ports?!
Generally :
1. Removing the headphone jack?!? Why? It saved almost no space worth worrying about and pissed a lot of people off.
2. Magsafe. It was a brilliant little feature that saved many an Apple product from ending up on the floor. Why get rid of it for USB-C.
Is Apple just letting some designer who hates ports dictate technical policy?
iPads: iOS is too limited for the advanced hardware that's in the iPad pro. It needs some kind of touch-friendly version of macOS to really make any use of it.
iOS:
It's too rigid and isn't changing with the times at all. The simple grid of icons that you have to shuffle around like a 1970s tile puzzle is really very limiting.
It also needs to open the door to a few things like other web browser rendering engines. The block on that seems absolutely stupid. Also the lack of any kind of access to the file system is completely stupid.
macOS:
1. Breaking age-old logical ways of doing things.
Why the hell did they feel the need to change the File > Save / Save As approach to saving things in so many Apple developed applications? I have ended up accidentally messing up versions and screwing things up because I didn't duplicate the file before making changes and suddenly realised that because there's no longer user-control over saving, it's just making changes to a live document. It's really unintuitive and breaks a very standard concept of how to deal with files.
2. iCloud integration - It's lacking transparency and too much is automatic. I have found that I have accidentally put stuff into the iCloud that I had never intended to. This included work documents which would be subject to data protection requirements. I was really annoyed that this was so easy to do.
I've also discovered that colleagues had put their entire Desktop into the iCloud without realising exactly what they'd agreed to.
3. iCloud lack of transparent access to the file system / inconsistent access to it anyway. It needs to just be a normal drive more like dropbox.