Is it his difficulty getting the dogs, training them to hunt coons, the death of Rubin, winning the hunting contest, or the grief of losing his dogs?
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Much of the beginning of the story is concerned with obtaining the dogs. Billy's character is developed through his grit and determination in earning enough money for the dogs. This forms the basis for our understanding of Billy as our protagonist. The other problems are dependent on Billy finally adopting Little Ann and Old Dan. The other problems that you mention are important; they are, however, dealt with as Billy matures. This question really is open for interpretation but I am inclined for the first one.
Really all the problems you wrote are correct! But the one for me is for sure losing his dogs! If you ever have lost a pet or anyone you know it hurts and you feel like you want to pass away with them. Yeah the death of Rubin was a big deal but they talked about that only for a little while. Sure Billy was thinking wasn't it my fault. And he might have thought about it but that was not a big effect on his life. Winning the contest was a super big thing! But I think you can answer that question yourself. Training them is important but it's something you have to do. I don't really see that as a "big problem" Getting the dogs would probably be my second choice as a big problem. He put a lot of hard work and effort into getting them. He saved and saved. It took him two years! I probably would have given up! That really shows some determination! But anyone's answer is correct! What do YOU think??