I would suggest you document the 3 experiences and send the lurkers a note - they need to pass this serious glitch to the IT team to get the glitches fixed.
The timeline sequence of display of Stays have been totally messed up in my account for a few weeks. Lurker was informed, and the description together with screen shots have been passed along to IT. It took 2 back and forth, but the issue was finally fixed last week. Now the display is in correct timeline sequence.
Back to the issue you have experienced, I canceled an AC Hotel thru Desktop 2 days ago. I have made screen shots on both the cancellation confirmation screen as well as the My Trip on both the current upcoming stays and the cancelled stays - the AC correctly dropped off from the Upcoming and showed up in the Cancelled. Yet, there is NO Cancellation Email ever come the next morning. I ended up calling the reservation line and had the rep sent me a Cancellation email which came in the format as if you request an email sent on your reservation, i.e. in Text format, not the usual format. Another several hours passed, like well over 24 hours after the cancellation, a "normal" cancellation email finally came.
I knew a lot of people having issues with the App cancellation, but now we are experiencing the issues on Desktop cancellation as well. This is very disconcerting. Therefore we should let the lurker know about the recurring issues. It is almost like they fix one issue then another issue popped up.