Dynamic post categories per user interest within newsletter

I am looking for a solution which allows me to create post category interest lists in wordpress for individual users, then install a newsletter plugin which might dynamically create newsletters based on the interests the users have selected during their account creation and/or durring the newsletter signup process.

For example, I write posts about topics A, B, C, D, and E, and send a monthly newsletter including all posts written in the last month. but John Doe is only interested in topics B, D, and E, and does not want to sift through all of the unwanted content to get to his interests. Rather than sign up for 3 different newsletters and get 3 different emails, there should be a way for me to send him one dynamically generated email which includes Johns interests.

I cant find anything like this but I have a hard time believing something this simple doesn’t exist which talks to wordpress.

anyone have any leads?