1. Each individual service in AWS may be perfectly well designed, but there are now about 5000 services in AWS, which means there's 5000^2 possible interactions between services. Services interact in strange ways, and there's no visibility (and no documentation) into exactly how. You can write 5000 bug-free functions, but that doesn't mean you'll end up with a bug-free program.
2. The craftsmanship that goes into each element of the AWS console is poor. Controls don't work like I expect, and don't work like similar controls elsewhere. Error messages are terrible, or missing, and don't give any clue what is actually going on, or what secret AWS-specific trick I need to use to fix it. I've wasted hours of my life on those spinners because it's not even clear if an action will occur right away, in 30 seconds, or 30 minutes. What is one supposed to do when they click a button, wait a few minutes, go to lunch, and come back to see "at least one of the environment termination workflows failed"?
3. The documentation and support is lousy. I've asked a few questions on AWS's own forums, and never gotten any response at all. The above error message appears in exactly one forum post, and AWS finally got back to them after 2 weeks, and it was all done via PM so I learned nothing from it. I've used the 'Feedback' button, and when I get a reply, it feels like some combination of "it's your fault" and "you should have googled harder".
> designing, leading, and building the frontend for an AWS service
Designing the frontend for an AWS service doesn't help with the biggest problems. It's like designing a city by designing apartments and offices, with no thought given to roads or signs.
> The universal thinking within AWS is that people will ultimately use the API/CLI/SDK.
I can't understand this. If someone can't get the web console to work, they're not going to say "I know, I'll just write everything by hand with the API instead". The web console is essentially your landing page and your trial combined. Do all your "personas" consist of people who build for the web but never use the web? Or who try a service, and when they can't get it to work, they double down on it?