Honest question, for an average but improving player.... Is it better to be with a top organization on a B team or a smaller organization on their A team?
You shouldn't be looking at it through this prism. For someone as young as 4th grade, the most important metric will be having him be on a team where he will be happy and want to practice and play games. For some kids, this requires friends be on the team. For others, it may mean something else. Kids this age aren't necessarily logical. If they are not happy, than nothing else matters. It doesn't matter if you think its the perfect team for him.
Also, as others have said, quality of coaching is very important. So will be playing time. Winning and losing matters also just to the extent that very few kids will be happy on a team that loses often. Travel time to practice and other logistics are also important. Some teams have outrageous fees, some don't. Also, its important that your kid not be an outlier. Being the best or worst on the team is not usually optimum.
All of this is more important than whether the team is the top team at the club or not.
