That motor and stock controller will run on 10 ah. No hills helps, and you'll have 8 mile range for sure. But the battery will be under considerable strain, often pulling 2c when leaving the stop sign. This will shorten it's lifespan for sure. But that doesn't mean it will fail in one season. It doesn't mean it couldn't fail in one season either. It's a matter of luck in a way. But in a pack tht small, each section is just two cells paralelled. So one weak cell and you are down 50%. In a 20 ah pack one weak cell and you are down 25%. So with the smaller packs, your luck of the draw that all the cells in the pack are perfect becomes more crucial. There will be more pull on any weak cells, and they will die fast in the small pack. So it's just a situation where the larger pack has you less dependent on each and every cell being really perfect.
15 ah is a good compromise. I have a 48v 15 ah that I have been running on similar wattage motors for almost two years now, and it's fine. I expect it to last at least as long as my first ping did, which was 700 cycles. It died only because I made a mistake in the end. Left it on a bike with the controller on for a month.
I would say go ahead and get the 36v 15 ah. You will have just about enough range to go about 16 miles, and charging every 12 miles or so would be best.