I wonder if MS acquired Skype today (i.e. "The New Microsoft") whether they'd have been more successful.
WhatsApp will probably face similar problems in 5-10 years, if they want to maintain compatibility with the myriad of clients they have in the wild.
They don't. They just announced dropping support for Blackberry and S60.
It's very interesting seeing the seamless merger of Skype into the Messaging, People, and Phone apps in Windows 10. Having finally figured out the new Windows 10 Skype Video app I realized that I could uninstall the classic desktop app and the Windows 8 version of Skype mobile that is (weirdly) still in the Windows Store on mobile as if it is still a useful app (and in which case it is not), unlike its short-lived tablet/desktop counterpart.
You can still see some of the uneven edges: the reason I had to figure out the Skype Video app was that it is the only one that currently supports accepting or making Skype contact requests, before you can link them in People. (I presume that sort of functionality should eventually merge in the People app more directly?) Also, there's still that slight friction between traditional Skype accounts and using Microsoft accounts for Skype that I'm unsure if there will ever be a clean fix.
I think that the "Skype Video" should be named something like Videophone to better align with brand-less Messaging, Phone app names, but that's a marketing quibble.
I do like the way that SMS messaging and Skype messaging interleave in the Messaging app now. It's nice having only one app for that. I wish it supported merging in Facebook's Messenger as well, but I realize that won't happen for many, many reasons.
As for Skype for Business, I think it's been solid since its Lync-branded days. I'm curious if they can get the sort of "platform leverage" we are seeing on the consumer side of things, but it doesn't necessarily need it. If they make it more Slack-like, that could be interesting.
Microsoft also owns GroupMe (www.groupme.com) and that solution has been pretty cool as well. I was surprised to find how focused Microsoft has quietly become on messaging products.
As an aside, this is regular old Skype, I've heard it being said that "Skype for Business" is a completely different program.
While I personally don't use the chat functionality that often anymore, the few times I have used it (say when an interview was being done over Skype), it worked ok but I realize that is hardly a high-use model. I agree that other messaging solutions such as Hangouts, HipChat, Slack, GroupMe, and etc. appear to perform much more seamlessly without needing to be aware of idiosyncrasies.
It is possible that the skype team has a different standard, different priorities imposed by the managers.