ARMember-Digital Download plugin is an easy-to-use, reliable WordPress plugin that allows you to upload various types of files OR add external file URL for download by users and set various kind of permission on it like which role users/plan users/etc. can download it.
By using this plugin, you can create shortcode for each download file. By placing this shortcode anywhere, you can place download link for specific users on front end. Also you can keep track of all downloads like which file is downloaded from which IP address, by which user at what datetime.
Also you will be able to set file download limit on each download based on user plan like you can allow plan A users maximum X downloads in a day/week/month/year.