The language wasn't that bad. Classes without inheritance -- that's the new hotness these days!
Since you lumped in VB.NET in there you're definitely past the prime era and oddly I agree that VB.NET is horrible while I still think VB, for the time, was perfectly reasonable. It certainly has less gotchas than JavaScript.
Considering that I spent (and still do spend) most of my afternoons with Haskell and F#, it was a bit of a shock and an experience that I don't remember fondly at all heh
One thing I would correct is that VB does not have extremely loose typing. VB is strongly typed with one exception: the variant type that could hold any other type (kinda like "object" in Java/C# but implemented like a union).
[0] https://github.com/Soldat/polyworks/blob/37aaf471646fe4773e6...
I can see that the tooling might've been great and all, but the language is seriously just horrible. And as for VB.NET, my experience was that the bearable parts were the ones it inherited from the .NET and C#. It might've been fine for prototypes, but at least IME prototypes never stay that, they get swamped with features and a few years down the line you have a Frankenstein's monster of badly thought out features struggling to interact with each other... except with VB, all of that is mixed in a soup of On Error Resume Next. I don't really see how anyone would put up with that in 2022