So, let's start with a pretty basic applications in a straight ahead sort of style, first by playing the 5-stroke roll as it's often notated in books:
Next, trade fours with yourself, preferably with a metronome, or better yet, a record. Four bars of time, and four bars of 5-stroke roll as written above. For now keep your feet going while you "solo", like so:
There are infinite possibilities here when it comes to orchestration, but if this concept is new to you or your student let's just start by keeping all the double strokes on the snare and moving the single strokes to the toms; right hand to the floor tom, left hand to the mounted tom:
One of the things with rudiments that I don't think is immediately obvious to students is the idea of permutation. Keep in mind that a 5-stroke roll is just that - five strokes; two double strokes and a single stroke. There's nothing to say that it has to be played exactly as written above. We can start it anywhere in the bar to create new rhythmic ideas. With that in mind, try starting with the single stroke, and also starting on the upbeats. For the sake of clarity I've left out the bass drum and hi-hat notation, but I'd still recommend keeping them in for now.
Let's play the single strokes as an eighth note rather than a quarter note for a longer phrase. This will create a hemiola that will naturally resolve after three bars. Try playing these in both four and eight bar phrases. For four bar phrases you'll play measures 1, 2 and 3, and then measure 1 again.
And lastly (for now) turn the whole thing into triplets:
The examples here are just the tip of the iceberg as the possibilities really are endless. Of course I recommend you put in your Wilcoxon time, and if you really want to go deeper into this stuff check out Joe Morello's book Rudimental Jazz.
Here's the whole sheet laid out. Please feel free to get in touch if you'd like a PDF copy.