I fought with similar gdb issues for a while. My case was having lots of threads spawned that executed few functions and then exited.
It appears if a thread exits too fast and there's lots of these happening sometimes gdb cannot keep up and when it fails, it fails with style as in crashes :) I think it tries to attach to a thread that is already done as per the error message.
I see this as an issue in gdb 6.5 to 7.6 and still happening. Did not try with older versions.
My advice is look for this use case or similar. Once I changed my design to have a thread serving a queue of requests gdb works flawlessly.
Design wise is healthier to have already created threads that digest actions than always spawning new threads.
Still same code debugs without a problem on Visual Studio so I do have to say that is a small disappointment to me with regards to gdb.
I use Eclipse and looking at the GDB traces (usually enabled by default) will give you a better hint of where GDB fails. One of the buttons on the console shows you the GDB trace.