Good beginner motorcycle for about $1000-$1500?

The type of terrain that you describe says you need a dual sport motorcycle. However, size is no indication of a motorcycles ability to climb. The Honda rebel 250cc does very well at climbing since it has low gears. I have taken the rebel up some inclines that are difficult to walk up. Along those lines, if you can't afford a dual sport, the Yamaha 250cc v-star or suzuki gz250 would also do very well. The Gs 500 is not so good at climbing since its geared a little higher for top speed rather than hill climbing and those sport rated tires don't do so good. But, if you will only have that type of terrain when going home or leaving home you can learn to keep the rpms up. But, generally a cruiser will do better than a sportbike for what you describe.