Actually your checkboxes are named chckIEP and chckPsy
I would address this by adding the bookmark name and text values to the tag and ControlTipText properties on the relevant userform checkboxes. Then you implement the following code changes to the userform code - amend OK_Click and add the PopulateBM function.
Code:
Private Sub OK_Click()
Application.ScreenUpdating = False
With ActiveDocument
.Bookmarks("bmDate").Range.Text = txtDate.Value
.Bookmarks("bmName").Range.Text = txtName.Value
.Bookmarks("bmUCI").Range.Text = txtUCI.Value
.Bookmarks("bmDOB").Range.Text = txtDOB.Value
.Bookmarks("bmSchool").Range.Text = txtSchool.Value
.Bookmarks("bmIEPY").Range.Text = txtIEPY.Value
.Bookmarks("bmPsyY").Range.Text = txtPsyY.Value
.Bookmarks("bmSC").Range.Text = txtSC.Value
PopulateBM Me.chckIEP
PopulateBM Me.chckPsy
End With
Application.ScreenUpdating = True
Unload Me
End Sub
Function PopulateBM(aCtl As Control)
Dim sBkmk As String, sText As String
sBkmk = aCtl.Tag
sText = aCtl.ControlTipText
With ActiveDocument
If .Bookmarks.Exists(sBkmk) Then
If aCtl Then
.Bookmarks(sBkmk).Range.Text = sText
Else
.Bookmarks(sBkmk).Range.Text = ""
End If
End If
End With
End Function