524577 PHP Dynamic Content Newsletter

I have a plugin that will send newsletters to members of my site. I need the following mods to it: 1) I can already send mail based on user level but I need to be able to filter mailing based on profile categories also. 2) I need to be send dynamic info of my core product (links) to the email list. I want to be able to select Links from to be included using a simple checkbox and specify how many times the link will show on newsletter, then once it has run X times, it becomes UN checked.