CCRC Entry fee Medical Deduction

This year I bought into CCRC in 2023.  I expect to get documentation early next year that will tell me what I can deduct for medical.  I expect this will allow me to itemize in 2023.  Does this make sense?  If so, can I itemize for all items?  Additional medical expense like prescription drugs?  Donations?  Are there any other deductions I should consider this year since I can itemize?  I would like to donate a car vs selling.  Does this make sense?  Sorry for the mind dump.