If you want to keep 14 days, regardless of the number of versions, then simply tell CloudBerry to Delete Versions Older than 14 Days.

If you want to ensure the most recent backup of a file is always kept in cloud storage, then check Always Keep the Last Version - otherwise after 14 days all backups will be removed if the file did not have a reason to be backed up because it did not change.

If you use Versions as mentioned in your post, then you will also keep up to 14 versions within that 14 day period. As an example, if you backed up every 15 minutes and made changes every 15 minutes, the file would be backed up every time and you'd only have the last 3.5 hours of backups in storage.

If you want to delete backups of files that were deleted locally, then make sure select that option. But if you want to keep backups of deleted files just in case you ever need them, then leave that section unchecked and check the option (mentioned above) to Always Keep the Last version.