I'm considering the part that says "GDB and LLDB pain me greatly". This project both says "I'm doing this for fun" and "the state of the art is bad, and I'm trying to fix it", so this is a fair question.
GDB is great. He says it crashes a lot, and cannot interpret some of his types. Maybe that's his experience, but I haven't had those issues after literally decades of using gdb. Some bug reports would be nice.
After literally decades of occasionally dipping into GDB only to quickly remember why I would rather use no debugger at all than that, it's hard to imagine what you could mean by "great". What are you comparing it to?
Decades for me as well, and we’ve had very different experiences : gdb is very powerful , but the user experience is atrocious and it does crash a lot.
To be fair, in a number of cases the type issues I had were not gdb’s fault but bad DWARF produced by the compiler.
