GitHub: https://github.com/hi5/TCSyncComments
Reference: I posted a suggestion for a "Manual option to copy file comment descript.ion F5/F6, Shift+F5" here viewtopic.php?f=14&t=72059
Until such a feature is added to TC I will use this AutoHotkey script

Note that the script "as is" works for me and I don't plan to add new features or change how it works apart from (obvious) bug-fixes or easy to add/change suggestions.
To better understand the purpose let me briefly describe how I use file comments:
(Also check the demo animation in the GH Repo)
I have "Copy comments with files" turned off in the TC configuration.
I only use comments in specific project folders, so for all other folders and file operations I don't want to copy or move the file comments from descript.ion to a new location or keep track of renamed files.
For specific projects I place files in a folder. During the project I add comments to keep track of the status of each file (draft, commentary, pre-processing, final version, etc).
The final stage of such projects can be that the data from these files have to be processed in a specific order. At that time I rename each file to start with a number (01, 02, etc). Or sometimes I copy some of the original files to a backup folder, either keeping the original name or renamed.
So "Cherry.txt" is renamed to "01_Cherry.txt" or copied to "backup\Cherry.txt", "backup\Cherry_org.txt"
At that point the file comment for "Cherry.txt" is "lost" due to the my preference to not "Copy comments with files".

BUT in such cases I DO want to keep/copy the file comments for some or all of the renamed or copied files. Enter TCSyncComments

TCSyncComments is a AutoHotkey script to copy file comments (descript.ion format only) from:
- Source to Target folder (identical or partial matching file names)
- Current Folder (useful for renamed files)
- Selected or All Files
It can try to find matching file names using Sift Ngram - so "01_Cherry.txt" will match with "Cherry.txt"

This script will not copy, move or alter (selected) files - only the comments stored or added to a descript.ion
TCSyncComments copies file comments it can find in descript.ion or try to add "new" ones based on file name "match",
either in the current or target folder. (Target folder is source of descript.ion to use)
Note: it does not (yet) try to use the "set type" file encoding from TC as I only use "dos text" (0-9, Aa-Zz chars) in my comments.
Demo
Image: https://raw.githubusercontent.com/hi5/_resources/master/tctest1.gif