It's been a long time, but I've come back here to get some knowledge from those who are a bit further on the journey.
Here's the question/situation. Last year we decided that the academics at my son's school sucked so bad we couldn't take it anymore and enrolled him in a private school. It's not cheap and I hate like hell paying tuition on top of taxes, but the difference for my son has been nothing short of dramatic.
The new school has some sports, but doesn't have 2 of the 3 he plays (baseball, basketball, and football). They do have a participation agreement with the local public school for baseball and football but since we don't reside in that district they are trying to keep him out of football this coming fall. That's not a big deal and he can take/leave football since he likes basketball and baseball much better.
Baseball however is his favorite and best sport. If we keep him in this school and the other school manages to dodge the agreement with his new school, he would only play rec and Legion ball but no school ball. In the grand scheme would that matter as far as baseball only?
The baseball teams (actually all sports) at his home school are and have been dreadful for a long time. One thing he does like about the new school is that they are 100% behind any sport they do offer and have a winning tradition unlike his old school.