peach ...
First I would recommend you check this link to another thread (under After High School forum) from a while back ...
http://hsbaseballweb.com/eve/forums?a=tpc&s=5316041581&f=9886003481&m=737105315If you still have questions about $$, come back on this thread and we will see what we can do for you.
As for the length of the season ... most summer wood bat leagues start in early to mid June and go till early August. Several leagues have their own post season tournament (such as the Cape) which keeps the players there about another week. Quite a few leagues participate in national tournaments (such as that sponsered by the NBC whose "world series" is in Wichita each year). That really drags out for some of the players because teams going to the NBC world series can take players from other teams in their league (similar to Connie Mack, etc.)
Hope that helps.