This may just be my lack of experience in Drupal talking (I've got plenty of experience in PHP, just not Drupal), but I put a pretty decent amount of thought into the matter and even mocked up simple prototypes just to see if there was something I was missing.
I have had an absolutely terrible experience with it, which sadly isn't unique amongst these big PHP projects.
My primary job for the last 2 years has been developing a Drupal site for a group of daily newspapers with monthly page views in the low 8 figures.
We were in a situation where we had to get a site up quickly (Our small group was bought off from a much larger conglomerate, so the huge $$$$ Java system we had been using
went away). Drupal allows us to get a tolerable site up in about 3 months, and a much better site up about 6 months later. Have there been pain points? Sure. But if we'd used anything else there's no way we would have been on our feet nearly as quickly.
Are we investigating other options? Of course, if I wasn't I wouldn't be doing my job. There's a part of me that would love to rewrite the whole thing in Rails or Django. That would be a huge undertaking though.
We've had different experiences, but I wouldn't touch it with a 10' bargepole, not any more. And I'm glad I've been managing to encourage my boss to start moving away from it. The only positive thing I've been able to take from it is a list of things never to do in my own code.
Like I say, it's not just Drupal. It's a side-effect of over-complication in the name of simplicity, and trying to run in parallel a system that makes it easy for non-devs to use. It's a recipe for disaster if you want lean, maintainable code.
Oh, and it causes performance problems too.
Understatement of the year so far.
I love Drupal, but since there's no bright line separating configuration and content, rolling features up from a dev environment to staging to live can sometimes be a nightmare, particularly if the Features and Strongarm modules don't have you covered.
Drupal is extremely powerful, but would be a nightmare for users used to the WP platform.
Drupal does have wysiwyg implemented as a module http://drupal.org/project/wysiwyg (actually several competing editors are possible),
Drupal also can do automated updates, though I wouldn't advise it. Drush works for it, http://drupal.org/project/drush and a lot of people use it with great success. You would want a carefully vetted rollback plan though. The better road is to forgo updates other than security until scheduled maintenance or a MUST have feature is present. The GUI /update process is actually quite nice if you've set everything up properly.
The thing about Drupal is doing everything doesn't have to be painful, but if you've approached it in a "non-Drupal" way it can get bad quickly. Drupal is complex and the hand off to a customer is never easy with complex software. Have you tried the same with Plone?