Yes, VB as a language was terrible, in the same way that almost every BASIC is "terrible". There were some old ideas in the BASIC heritage that didn't age well. IIRC, it wasn't until VB6 that you no longer had to prefix string variables with $. But by that point there was an ecosystem issue of old documentation, legacy code, etc.

WinForms absolutely captured most of the same feel of VB6 from strictly the perspective of the tooling. I think it took a while to really catch on because, being a from-scratch rewrite, it took a while to gain complete feature parity, while also lacking the subcomponent market that a lot of VB6 projects had grown to rely on.

But then, GUI requirements also evolved. HighDPI displays, internationalization, accessibility, bigger and bigger projects needing better organizational methods. You can solve most of these issues in WinForms by being super fastidious about componentization, but it's not the happy path of just double-click-on-the-form-designer.

All of the XAML-based GUI systems that Microsoft developed since then have tried to invert that issue. They wanted to start people off by being considerate of componentization. Unfortunately, it came at the sacrifice of the usability of the tools.