I find the approach of http://www.itagsoftware.com/ the best, and the tags are stored with the file (but this only tags photo’s and video) and then a search is done to build a tag cloud/index. Moving files (or computers) your tags still exist.

The mac’s have a number that work this way, http://tagamac.com/ but I can’t find a PC equivalent??

Here is my ideal application:
The most important feature of such an app for me, is that it blends with the OS. This TaggedFrog seems to have a nice main program interface for browsing tags etc, BUT if I have to start a program just to tag one single file, I probably won’t care to tag stuff often enough, and then the application has no use.
- Yes, a context menu could be a solution if it cascades (only takes up 1 slot on top of context menu), and isn’t slow.
- However, I picture having an additional toolbar or maybe 2-3 buttons one can add to existing Explorer toolbars:
* Button 1: Filter contents of a folder by tag, which gives a dropdown of every tag present in that folder or subfolder. Sort by standard Explorer sort-setting.
* Button 2: New item in “Sort by”, namely “Sort by tag”. Same behaviour as clicking the tag column header. If one could sort by tag primarily, and then sort by type/name secondly it would be perfect.
* Textfield 1: A mini input field which can be used for both filtering and adding tags. Choose to either filter folder contents (by tag or filename) and match against the entered text, or choose to add the entered text as tag for selected files/folders

The additional Explorer column for tags is also a must, and I feel it should list several tags for each file/folder. These tags could be hyperlinked so clicking a tag filters the view by that tag. Users can define the importance of tags, so for files the tags will be listed by importance, whilst for folders which tags are displayed first in the tag-column is determined by usage/frequency of each tag in the (sub)folder. I realize that this does require a lot of querying, but the FolderSize project ( http://foldersize.sourceforge.net ) does this in a smart way with a running service which I think can be used by this app as well.

If you had all these features working seamlessly, I would definately be willing to donate for maintaining it (and probably buy it, but this is a freeware site after all).

The thing about HobComment though is that it has no database-style functions, such as filtering or searching. If I wanted all the files that I have “tagged” by certain keyword in the comments section I cannot retrieve them.