I still cant believe that this is not already a built in option with some program.
-questorfla
The reason for the difficulty is Windows file system does not support comments. I'm told DEC file system CMS had this feature. I suspect the database file system Windows Longhorn was supposed to feature, but never did, was a CMS port to Windows.
So what it means is you have to do things like create external files to hold the comments or annotations. When you copy a file using Explorer or command line, the system knows nothing about annotations so the comment does not travel with the file.
In fact I wrote a shell extension called TipOff for 32 bit Windows that showed the comment when you hovered the mouse over the file in Explorer. It did this for certain archive file types such as zip rar tar etc.. Unfortunately for your purpose I don't know if there is any way to copy a tooltip display to clipboard so that you could launch it in the browser.
https://www.donation....msg266872#msg266872The Property Page Tab in the screen shot is what you were talking about afa typing or pasting in data. It seems more convenient than it is I can tell you after testing these shell extensions. It gets tedious quickly. But ok for commenting downloads assuming you don't use it for hundreds of files a day.

Note the link in the post is dead. I still have the program but it only works in 32 bit Windows.
An easier approach may be to keep EditPadLite open and paste the link into it. The editor makes the link clickable. Then you could just put the name of the file on the next line and do control f search.
For the TreePad file approach I have a program on my page
TreePadGen that creates a TreePad file(.hjt) with a blank node for each file in a folder. At least it would save typing or pasting in the names of all your downloads.