I honestly have no clue what you're getting at with your first paragraph. Email hasn't changed very much in the last fifteen or more years, so I'm not sure what changes the "Web 2.0 people" made you're referring to, your examples are pretty odd ("scan other addresses" what?). Also keeping a backup of deleted messages for a period of time is standard industry practice and has been since before I or Linux were even born.
As far as MS Outlook and standards: That little rant reads like it was written about web-browsers and you just replaced "Internet Explorer" with "MS Outlook." MS Outlook uses a fairly standard implementation of IMAP/POP3/SMTP and has since forever. Microsoft have their own ActiveSync mechanism which isn't a standard, but no competing solutions have really appeared which compete with ActiveSync (and replace IMAP) so while you could blame them, you could also blame the complete lack of innovation in this space.
I can't speak for Outlook's performance at the MTA level, but the user-facing parts break all sorts of expectations I have from twenty years of standards-compliant email. For instance---just at the tip of a very large iceberg---they have invented a completely new way of representing name/email pairs in the header fields, with the list separator being the semicolon, the email delimiter being square brackets, and a few other things. If I have a list of email addresses from some other source, I have to reformat it just to use it in Outlook.
I have to use Outlook Web Access at work (no alternatives), which is even worse than regular Outlook, and I'm keeping a list of all the ways its user-facing interface is broken. I left the list at work or I'd be able to rant for pages right now.
It used to be that you kept your email private and didn't share the details with anyone. Now, you have to be very, very careful about other 3rd parties trying to access your email - or otherwise convince you that they should be trusted with managing your email account so that they can fulfil their business purpose of building a social tree.
This wasn't really an issue pre-Web2.0. But now with all the effort to construct billion dollar social networks, its quite a common thing for people to just hand over the keys to their email and ignore the risks.
Back in the 80's and 90's, your email password wasn't something you ever shared. Nowadays, its almost like the other way around.
Oh .. as for your criticism of my 'rant', well I suppose I could also finger GMail for the mess that email is in these days ..
It's also the worst, Widnows IMAP client I've found, period. I suspect it doesn't implement caching in an intelligent way. I long for a functional version of Evolution for Windows.
As far as MS Outlook and standards: That little rant reads like it was written about web-browsers and you just replaced "Internet Explorer" with "MS Outlook." MS Outlook uses a fairly standard implementation of IMAP/POP3/SMTP and has since forever. Microsoft have their own ActiveSync mechanism which isn't a standard, but no competing solutions have really appeared which compete with ActiveSync (and replace IMAP) so while you could blame them, you could also blame the complete lack of innovation in this space.