Sincere question: How is Skype not a near-real time async messaging system? What features is it missing that 'a messaging system should have'?

Reliable message delivery, reliable history and history search.

can't you history search through outlook under the 'conversation history' folder? (or click the 'see more in outlook' hyperlink on skype.) Although yes, it's not built in to the skype app UI itself. And that would be nice.

We have lync as the corporate rubbish system (all corporate systems are rubbish)

From what I can see It's pot luck which machine a message will go on The ios client is terrible There's no channels There's no history half the time (if it pops up in webmail for example), if there is, it's client based not server based

We also use irccloud and slack, they are actually useful - irccloud from a standards base, slack from an ease of use. I don't understand why people have so many problems with them.

That renaming Lync -> Skype is still very confusing.