For anyone with similar challenges, I solved this one without set analysis. My approach here was:
Sum Points for each user over the date range currently selected with this:
To get approximate monthly values, the above becomes this:
Then I compare the result to my variable that determines how many points is needed for someone to be a VIP and when true assign a value of 1 which I then sum over:
This is probably more expensive than a set analysis solution but it's working.