Hi Jason,
Sorry for the delay. "Iterating over the checkboxes" implies writing code. There may be a way to do it using an xpath, but code may actually be simpler (and easier to debug). Unfortunately, we don't have time to write code snippets for everyone these days but if you want to retain us for a small fee, let me know.
Patrick Halstead [InfoPath MVP]
InfoPathDev
Patrick Halstead
Project Manager at Qdabra