What do I not like about Skype?

Its lukewarm position in my life. That's a completely vain-sounding complaint.

I don't like that it's a standalone program and I have to schedule calls with people. I want to videochat on a whim, as part of my social experience (what Hangouts was supposed to differentiate on all along).

This depends on your use pattern. I never leave Skype open, because my friends never do. So it’s just a weak shell of a social network and one more social service I would rather not have to keep track of. And maybe at some point everyone did leave Skype open, but Skype never attempted to go beyond its functionality as a basic communication service, and when our modern generation of social services came up which allowed for much richer interaction and a relational "permanence", Skype isn't so compelling. Skype is a utility that I open when I need to have a meeting with someone, and that's no fun.

Skype, and most messaging/calling apps, grow when more people start using them and grow even more when even more people start using them. That's an inherency of being a social service.

In parallel, when people stop treating Skype as something worth dedicating their time to, others close in the network also stop treating it as something worth dedicating their time to. Skype will remain a competent tool for audio/video calls with strangers or acquaintances because of its wide adoption, but adoption or userbase is a different game from engagement, and a social product that doesn't see engagement from its users becomes even less engaging for remaining users. I'm guessing Microsoft will finally try to give it more integration, but even if Microsoft were to attempt some kind of social product, Skype would not be a suitable place to start because it has little ties with Microsoft's core offerings.

I, of course, am speaking from my corner of Skype's massive network. I am a 19 year-old, Millennial -- may or may not be typical. I have no doubt other areas of Skype's network are thriving or maybe even growing. But for me, this is why I don't like Skype and it's bigger than any issue I have with its functionality or interface.

I'm not totally intimate with Skype's corporate history, but it changed hands multiple times and is profitable with a big userbase so I fear that their innovation has been sucked out of them.

Everything leads to everything else.