Hi Leo,
You definitely have some missing files. It is very odd that install logs do not show any issues. Almost looks like something cleaned up some files after CCS installation. See attached report.html that contains listing of files that are missing on your system. Missing files are installed by a single component, thus in theory you should be able to just re-run that single component installer to get missing files. If you have a complete CCS v5 install .zip file, then you would need to unzip contents of this file.
\featurerepo\binary\com.ti.ccstudio.debugserver.win32_root_5.5.0.400
then run ti_dspack_ibsetup_5.5.0.400.exe file that is inside of above .zip archive (the extension is not there, but you can just rename the file). Specify C:\ti\ccsv5 as installation directory if your CCS is installed in default directory.
(Please visit the site to view this file)