Well, after talking with him, we're going to go ahead and get the two-player Legion and Circle box. Seems the best buy for our money. Has over double the model count of what normal starting boxes seem to have for both sides.
Legion is a great starting set, as most of the core rules don't apply to their units. Cuts down on the learning time.
Circle is a fun faction and has, in my opinion, the nicest models in the whole range. Just be prepared for lots of movement powers and buy some monoliths.