Hey Chris. I like your setup. I've had my eye on the Otter Medium box for a while. I wish someone near here would stock one. Shipping on those things is a real downside. Still, I think I just may have to order one soon, for the coming season. I agree with you about keeping the gear on the machine. If the conditions are right, I leave my sled and shelter in the truck and still have everything I need for a day of fishing.
One thing I did a few years back was to purchase an enclosed trailer that would carry my wheeler and all the gear. Best thing I ever did for my icefishing gear.