You are probably pretty awesome at setting things up. I am not. I tried GDB, golang and windows as a combination and its an exercise in torture.
That's true, I am great at setting things up... but Go+GDB was zero set up. `go build` then `gdb ${executable_file}`, and nothing else. I suspect that it's Windows being in the mix that gave you trouble?
In Mac at least you can't just do that, you need to create yourself a certificate and sign GDB. Took me a while too.
Just an FYI, you can use MacPorts to `sudo port install gdb`, and it installs gdb as 'ggdb' without the signing mess. To use with ddd invoke as `ddd --debugger ggdb` and it works like a charm.