Checkboxes are in "input" only feature. said another way you cannot have checkbox AND a formula in a cell at the same time. You can conditionally print a check character by using the following:

A1=CHAR(10003)
Now how to apply this?
Let's start with one possible solution. Here's an overview:

I named the table on the left "Term Start", the one on the right "Final Schedule" and omitted the row that you merged-- merged rows cause problems an I avoid them.
Let's start with the table on the left "Term Start":

I added an extra column which you can hide later:
C2=IF(A2=TRUE, B2, "")
select C2 and fill down
Now for the table "Final Schedule":

I did not want to type in (or copy paste the repeated dates) so I took the liberty of automating that based on the my observation that they repeated in groups of 8.
B2=OFFSET(Term Start :: $B$2, FLOOR((ROW()-2), 8)/8, 0, 1, 1)
A2=IFERROR(IF(MATCH(B2,Term Start :: $C,0), CHAR(10003), ""), "")
select A2 and B2 and fill down as needed.
I hope this helps