[saagarjha]

I don't know if you have looked at LLDB but when it evaluates (non-trivial) expressions it does actually compile and link code into the inferior's address space. One of the major selling points when it came out was that you could write "real code compiled by a a real compiler (LLVM)" rather than whatever ad-hoc thing that GDB knows how to do. In theory this gave better support out of the box for things that can't be represented with pointer dereferences or whatever most debuggers support for their data visualization. The downside is that LLDB is extremely slow, and it still fails a lot when dealing with templated types because it will claim (whether honestly or not) that the specialization it wants is not present. And it doesn't look at your source code to generate a new one, which would be an excellent showcase of the LLVM stack, but I guess a bridge too far for a debugger :/

For your thing: I think you can get pretty far with what you're doing, but I do want to point out that just the standard types will probably work for Rust but in C++ ever nontrivial project has their own standard library. Most also hide their data behind a void *impl or whatever so no debugger knows how to deal with it out of the box. I don't expect you to parse the codebase for operator[] or whatever but I think you'd ideally want a simple DSL for building pretty printers, with maybe memory reads and conditionals, plus some access to debug info (e.g. casts and offsetof). I don't think that would be too awful for complexity or performance.