Hey, sure. Here’s a proof of concept app. It’s doable in the free version except you’re going to run into a 1000 row limit on the interactions table, probably within a year with so many people you’re tracking. So you might have to periodically archive some of the data.
Here’s the app, two tables:
Counselor column on the communications table:
Making that should automatically create the has-many Communications column on People:
With that relation in place, the rollup should work with the has-many Communications column as the source, and Data as the field on the Communications table.