Have you tried the SdConfigEx utility in the following location:
- <CCS_Install_Dir>\ccsv5\ccs_base\emulation\specdig\sdconfigex\SdConfigEx.exe
It's not the most intuitive utility. Basically you click the icon that's a checkmark. Then try clicking the checkmark with "EMU" behind it.
You may also try going under 510 -> XDS510USB-PLUS and trying out the "Pulse TRST on startup" option. You might have better luck with that option.