Transferring to a different private high school

When is the best time to start the private high school transfer process? My child did not get their first choices of high schools and would like to have the possibility to transfer to a different school if they end up finding that the current school is not the best fit -- too big, etc.    I believe we received some bad advice during the middle school process and the results were devastating.   I would like my child  to have a good chance if they choose to pursue a different school.  Unfortunately, the process begins now, just as school is barely in session.  I don't want to seem too anxious -- asking for recommendations from teachers who don't even know my child -- they barely started 9th grade but the visits, inquiries, recommendations start now or soon. My plan is to get all of the foundation stuff in place (like saving the visits and interviews until December or January), then check in with my child periodically and if, by Christmas, they feel that they want to try again, then we are not doing a lot of catching up.  And who knows, my child could really thrive at the current school so I don't want to mess with that possibility.  But I believe that if I don't do anything, then I will be caught off guard.  Has anyone gone through something similar?  Is it best to wait it out and then try after admissions season?  I don't know the right answer, but it doesn't seem like our middle school knew the right answer either, so I will welcome and appreciate all advice.

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