Steve,
I don't really understand what you are trying to do. Why are you creating the comboboxes with code?
Regardless, you are not going to get around the string length issue. It is what is and since you text and values are greater than 255 you are SOL there.
You can map the CCs to an XML part and use the CC events to alter the CC value. I've attached a demo document.
I left out a critical line of code in the attached file. Here is the affected/modified procedure:
Private Sub Document_ContentControlBeforeContentUpdate(ByVal ContentControl As ContentControl, Content As String)
Dim oNode As CustomXMLNode
With ContentControl
Select Case .Title
Case "ComboBox_Demo"
Set m_oXMLPart = ActiveDocument.CustomXMLParts.SelectByNamespace("http://gremaxey.mvps.org/demo").Item(1) 'Add this line
Set oNode = m_oXMLPart.SelectSingleNode("/ns0:Mapped_ComboBoxes[1]/ns0:ComboBox[1]")
Select Case .Range.Text
Case "A"
oNode.Text = "AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA" _
& "AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA" _
& "AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA"
Case "B"
oNode.Text = "BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB" _
& "BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB" _
& "BBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBBB"
End Select
End Select
End With
lbl_Exit:
Exit Sub
End Sub