What all parents need to realize is that you are not alone. You may make a decision for a specific reason only to find out later that the circumstances have changed.
My DD's first 2 years playing 12U travel,
we made decisions based upon information that, to my fault, was not thoroughly researched enough.
Doing my best to learn from past experiences, this time around.
My experience with tryout season is that is can be a big game of musical chairs,
and with so much in flux, it's very hard to get reliable information on: Tournament schedule, roster, coaching, open positions, anticipated pitching roster, etc.
Teams can be very cagey when you ask these hard questions.
So, in a lot of ways, you are forced to make somewhat of a leap of faith, and hope it works out for the best, when you have multiple offers.
But holding out for information and answers to your questions, and resisting the fear/urge to "sit down" too early when the music stops,
might be the better strategy. Maybe.