Counting true result test from check boxes

I am working on creating a lesson program tracking sheet. Students can pay for the month upfront but the teacher wants options to mark every time they teach a specific student. This was if for example in June the student only had 2 lessons the teacher would have checked off 2 boxes thus the student could have an additional 2 lessons in July.

VBA code: This is not returning a text of true or false for me to count.
Sub addMultipleCheckBoxes()

On Error Resume Next
Set wr = Application.Selection
Set wr = Application.InputBox("Select one Range that you want to add checkbox in:", "addMultipleCheckBoxes", wr.Address, Type:=8)
Set wsheet = Application.ActiveSheet

i = 1
For Each R In wr
With wsheet.CheckBoxes.Add(R.Left, R.Top, R.Width, R.Height)
With Selection
.Characters.Text = R.Value

.Caption = "Check Box" & i
i = i + 1
End With
End With
Next
wr.ClearContents
wr.Select
End Sub

Also this may not even be the best approach for such a practice. The user is not very computer savy so I am open to any suggestions. I figured a check box would be easier to fill then typing in words, etc.

No suggestions at all?