This app was inspired by both your random sound application and also your random sample application.

It makes sense to me for the spreadsheet/notes entry GUI to also control some of the actions so I am calling it the Action/Spreadsheet Entry GUI for the sake of this description.  So I guess that means there would be two parts of the GUI. The action/selection part and then the notes/entry part.

User Experience:  The Action/Spreadsheet Entry GUI pops up at user defined intervals/random intervals that allows user to select from a number of pre-loaded files from watch folder(s) similar to the Random Sample App.
-A hotkey/button can postpone the Action/Spreadsheet Entry GUI.
-A hotkey/button can re-populate the list.
-A hotkey/button to select from favorite folders.
-A hotkey/button to open spreadsheet
-Clicking on a file from the pre-load list will open that file and pull date/time and file information into the entry part of the GUI.
-Right clicking on file takes you to file location.

The entry portion of the GUI would provide a place to enter notes alongside the date, time and file name. I am imagining it having several fields.   Being able to edit the text that the app enters would be helpful to correct or clarify entries.

Settings:
-Set watch folder(s) for application to open/play.
-Set random intervals
-Set Postpone GUI time
-Set file selection bypass (just opens a random file without the pre-load/without entry)
-Set how many random files to “pre-load” in GUI. (like random sample app).   
-Set what file information, time, date etc is pulled into spreadsheet entry.
-Set save location for spreadsheet.
-Set hotkeys for app if that is possible. (launch, postpone file)
-Set file extensions (and maybe application to open file)
 
I am trying to imagine how the spreadsheet entry will work.  I am not sure if you had ideas about how you would do this.

Other thoughts:
-I am not sure if it would be possible for the user to define some short text entries in the settings, that could then be selected from a drop down menu for the spreadsheet entry.
-Move file to a different folder after it has been loaded.
-Setting to remember last location GUI opened on desktop
 
I am assuming that the files would be opened using Window’s default application associated with the file type, however, it could be helpful to set what program is used to open a file.  Then the faster program could be used if the default application is slower to load.  This also means that work in that default application at the time of launch is not affected.

That is all.  As I mentioned to you, this was inspired by your random sound and your random sample app.  I certainly will understand if any of this just is not possible or within the scope of what you want to take on.   

I know a number of people who use this software professionally in their firms. I am considering buying it.  Figured I would share it here.  Maybe others have experience with it.

https://www.bitsdujour.com/software/filecenter-dms/

I really like this application.  Very cool!

I am curious how difficult it would be to make this so that it could open other types of files (video, audio, documents) or even from a list of links. I am using this as a reminder to stretch and exercise during the day.  The sound triggers me to refer to a list of stretches/exercises I have as various different files on my PC.   It would be nice for the file to be pulled up from a list of different exercises or stretches I have videos, jpegs of the exercises/stretches I am suppose to do.

Even better if I could track which stretches I have done in a spreadsheet, though that seems like a different program all together.  This is a great help, just wondering how easy it would be to tweak to my use case.