Outlook on the Web - Mailbox Clean-up

In my organization I make a point of being positive about Microsoft's design of user interfaces to support our standard which has been Office 365 for many years.  In general the software suite has served us well but I am finding it increasingly difficult to justify the productivity costs arising from what seems to be decreasing consideration of usability factors in Microsoft design.

Outlook on the Web has been a source of continuous frustration.  Today was a day of particular exasperation for our CEO.  His objective was to simply move a large number of old email messages to the deleted folder.
  

1. His first option was to check the "Sweep" option which looked promising based on the name.  It is, however, inexplicably hard-coded to delete messages older than 10 days exactly.  Why hard-code it?   Didn't anyone in the usability review team ask whether the hard-coded design is flexible enough?  
   
   
2. Ok Sweep is a bust,  our CEO is a tech savvy guy so why not try the "Create Rule" option. That looks promising at first given you can set a target folder for an action (e.g. the deleted folder) and set a criteria for messages to selected based on "received before" a given date.  Then you see that Microsoft has designed the UI so that the before date selection is limited to the current date and future dates. Yup - you can set the rule to delete messages created before the future but you can't delete 2 year old messages ... cause who would want to do that.  Really?  Is it just me or don't people want to delete old messages and actually have an opportunity to look at new ones before they delete them?
   
   
3. Ok - strike 2 - Rules can't help.  Our CEO is s determined guy and accepted that automation for mail box clean-up was too much to ask for so the next option was to delete manually.  That seemed doable as it is possible select messages using the control on the left-hand-side of each message and then click delete.  There is also support for selecting a range of messages using Shift-Select. If you delete a handful of messages with this method it works.  Based on that result he next tried selecting a few hundred.  Still looks good - you will get a very reassuring message that you have deleted the count of messages you selected. And so we're off ... selecting and deleting messages until all 2,000 old messages are reportedly deleted.  .... and nothing is actually deleted.  The messages all return to the inbox except that first handful.  Is there a limitation on records that can be deleted at one time?  Maybe - but there is no message about it.  The confirmation method is not based on any code checking anything - its just a text response based on no evaluation of the underlying data.  No testing, no usability review.  

While the overall effect of these quality issues makes it feel like the software was specifically designed to disrespect the user's time - I don't suggest Microsoft set out to achieve that.  It is however the result - about an hour of time wasted by a senior executive without having accomplished anything.  

My sense is that MS has not traditionally had such a quality and usability problem in major products like Outlook. Is usability testing too much to ask for in the new world of inexpensive browser based subscription software?