VB1-6 encouraged classes. The fact that OO was not more popular in VB was a failure to communicate. VB.NET didn't add classes, it removed the anti-pattern that was grab-bag modules. Again, that's much more of a backwards compatibility problem than a CLR problem. The VB team
could have kept modules and still targeted the CLR, they just chose not to in the hopes of cleaning up some of the worst patterns in VB.
Just because you can "mechanically transform" code between two languages doesn't make them the same language. Compilation is a mechanical transformation to machine code, but you don't see anyone arguing C++ is the same language as Assembly.
(Did you ever look at the output of such mechanical transformations? The results were always weird, lacking proper idioms in the target language. Just like machine translations of spoken languages, I wouldn't rely on them without a lot of work to clean them up and verify them.)
Yes, VB.NET and C# share many (but not all!) components of the same AST, but so too now does F# as it is being brought over to the Roslyn compiler platform. Shared AST components also do not make a language "the same", because of that fun word "abstract" in AST. Just as most languages can be described in a BNF variant, fall into some variation of the category Context-Free Grammar, represent similar Pushdown Automata, etc. The underlying tools are very much the same across the vast spectrum of languages, but that doesn't mean all languages are the same/interchangeable.
Also, Visual Studio is a direct successor to the VB6 IDE. Visual Studio .NET shared a lot of code with that IDE. I'd be surprised if VS today didn't have at least some code inherited down the many years from that predecessor (certainly plenty of ghosts of it in source control). The VB6 IDE was considered "industrial-strength" in its time, too.
Given there's a free Community Edition of Visual Studio, and VB6 was never cheap, arguably the barriers to new developers to "just get to editing code" are at the lowest they've ever been, complexity or not. (Nostalgia is a weird fuzzy thing.)