Don't know to answer your question. It can be a million reasons for why your GDB install does not work. The GNU GDB is a 3rd party debugger, it was not made for this particular MCU. However, the TI debugger (IIRC a GDB customised by TI) should work flawlessly. Or at least that's how I remember the TI debugger from when I was fooling around with MSP430.
My recommendation would be to use a virtual machine (VM), and install inside that VM all the TI's proprietary toolchain/compilers from 10-20 years ago. They can be found and downloaded from the TI SW archives for free (so, do not install the latest/current SW, go for the versions that were in use while your MCU was at its peak selling). Licenses that used to be payed compiler license are now free to use (by TI, not talking about hacking, you can download the TI compilers full license from the TI SW archives, for free).
Those proprietary TI compiler and debuggers versions used to work better, and often produce smaller code than the most recent versions. AFAIK, older (upto v7 IIRC were GPL licensed anyway, a GNU/GCC toolchain which was heavily customized by TI, but this is fade memory and don't have any evidence right now, so don't quote me on it).
Anyways, install the old TI toolchain in a VM, then save the VM on your disks, and keep that VM and all the MSP430 devtools isolated (offline). If the TI SW was good enough 10-20 years ago, it is certainly just as good today for the same old MCUs.
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