I think GDB is a pain and it is even worse on the OS3.x department than the OS4.0 departement. Something definitely must be done about this since we seem to be at the mercy of GCC as our compiler of the day.
As a Mattathias Project developer, I think source level debugging software may need to come from the
LLVM project in the form of
CLANG. CLANG is a C, C++, Objective C, and Objective C++ development system for the Low-Level Virtual Machine. It's making rapid headway but only currently supports JIT compilation on PowerPC and Intel. It supports static compilation on others though.
Both LLVM and CLANG are under a BSD-like license so this may be a starting point for further development. Especially since CLANG is a library-oriented system designed for producing IDEs out of.
I've seen on the LLVM-Dev mailing list that somebody thinks LLVM needs a source-level debugger and is starting to work on one. This means that any compiler based on the LLVM bitcode can have source-level debugging without being tied to one processor family.
If things go well with the Mattathias Project, we'll be making a backend for either GCC or LLVM to run on the 68000 series also but we're kind of busy on our flexible parser design at the moment. Currently the Mattathias Project has 2 developers so we won't be able to make huge progress all at once but we'll do our best.
Questions? Comments? Derogatory remarks?