I've tried many variations and got very close with:
=IF(CONTAINS("Orientation", Course@row), INDEX({Course Start Date}, MATCH(Course@row, {Courses Dropdown Name}, 0)), "") - it only pulls when there is one selection provided in the multi-select dropdown and a "#NO MATCH" where there are more than one course selected.
We have 3 different classes every month with different start dates and want to capture the start date for that particular student.
Hope I've provided enough information to find a solution.