Try the following
1. for a single date in the OGM use 'Text to Speech Synthesis of Script' and set the script to
For %date% press 1
2. for multiple dates you will need to use plugins
a. create a plugin that scans the folder and creates a return variable like returnvar containing
For file1 press 1 For file2 press 2 For file3 press 3
where file1..filex are the filenames.
b. Again use 'Text to Speech Synthesis of Script' and set the script to
%returnvar%
c. You will need another plugin to handle the decoding of the key press to filename. Possibly each key press would run a separate OGM (say OGM1, OGM2 etc) which run a plugin accepting a parameter of the key number. The plugin would scan the folder for file x and play it.
Both plugins would need to be written as there is nothing existing.