Graham is correct about the bookmark position not 'including' the text so you couldn't revisit the dialog multiple times. To resolve this on my previous code, the function should be amended to...
Code:
Function PopulateBM(aCtl As Control)
Dim sBkmk As String, sText As String, aRng As Range
sBkmk = aCtl.Tag
sText = aCtl.ControlTipText
With ActiveDocument
If .Bookmarks.Exists(sBkmk) Then
Set aRng = .Bookmarks(sBkmk).Range
If aCtl Then
aRng.Text = sText
Else
aRng.Text = ""
End If
aRng.Bookmarks.Add sBkmk
End If
End With
End Function
You could then query the values in those bookmarks to prefill the status of both settings as part of the UserForm_Initialize macro.