So they have been working on uograding this since 2014? So far, the visible results seem a bit underwhelming for the invested time and effort. How big is the team? What am I missing here?

Well, the team is small, we're up to three whole devs now. Since 2014 we've been doing a lot of work o help bring our VT implementation up to par (to help enable WSL), as well as implementing new features such as 256/RGB color support, improved accessibility features, and we're even releasing a pty-like API for Windows.

Not only that, but since the team was founded we discovered that conhost was not the only console implementation in Windows, though it's the only one available on Desktop. There was a pretty massive undertaking to unify all the separate console implementations on different SKUs under one application, so that all of them would be improved at the same time. It didn't have a terrible lot of impact on the everyday developer, but it was important to help internal engineering efforts.

I don't use Windows mostly because the console experience is so bad. I'm sure there are many others like me. Your superiors should realize they have lost generations of developers because of this and dedicate the resources needed to fix it. How they haven't realized this yet, astounds me.

Use mintty (or wsltty for WSL). It's slow but it's good.

The Windows console really is rubbish, even after all these updates; don't bother with it.