What are you doing for breakfasts at the start of the day? Traditional cooked oats loaded with cream or yoghurt are probably the best value in terms of calories and dollars. He is obviously in slight energy deficit at the end of the day, and that might start with an inadequate breakfast.
Fats also play a pretty important role in delayed energy release later on in the day.
I know Machka finds the diet supplement Ensure a pretty good booster on long distance rides, and is available in places like WalMart in both liquid and powder form.
In the end, it comes down to mainitaining a balanced diet and a balanced energy intake compared with exertion during the day. Mayeb you should consider reducing the distances you do each day if the weight loss becomes more of a concern.
As a by-the-by, does he have any cravings during the day? And how are you and the rest of the family doing in terms of weight loss/gain/stabilisation?