It sounds like you’re aggregating some data onto a user record, then want to chart that aggregated data.
Skuid makes this sort of thing pretty simple compared to SF. If you wanted to see won opportunities by owner, you’d create a model with the opportunity object, use conditions to get the won opps, and group by owner and the calendar month of the created date (or whatever date you want to use). Use this model to create a chart and you’ll have data graphed by month and user.
