The tow/haul button is meant to be used when towing or hauling just exactly as the name implies. I use it at all times when towing my tt. The Allison seems to like it, runs a little cooler. On downhill runs if you just tap the brake once the trans does a fantastic job of holding that speed from that point on.
When I use truck to haul a load I generally do not use it. Usually when I am hauling it is on flat ground with loads that are not too heavy. If I do load it to the max and have to negotiate any grades then yes the tow/haul gets used.
I think you just need to play around with it and find out when it feels right to you.