Changing text in textbox once something is erased

[Rob123]

After rethinking the problem, the delete-watcher really wasn't necessary
Use your original program, and try this:

Dim keyWord As String
    Dim searchCount As Integer
    Dim notFinished As Boolean
 
Private Sub cmdAddNum_Click()
    searchCount = 0
    notFinished = True
    keyWord = " "
        
    Do While notFinished
        searchCount = searchCount + 1
        If InStr(1, txtDesign.Text, keyWord & GetRoman(searchCount) & ".") = 0 Then
            NextRoman = searchCount
            notFinished = False
        End If
    Loop
    
    NextAlpha = 0
    txtDesign.Text = txtDesign.Text & (GetRoman(NextRoman) & ". ")
    txtDesign.SelStart = Len(txtDesign.Text)
    txtDesign.SetFocus
End Sub

This will search for any missing numeral in the text.
Replace

keyWord = " "

with anything you choose which will be the identifier for the numeral.

As for the King George V. problem, this will only cause confusion if it is written as the 4th statement, and it will skip the 5th roman numeral.

If X is written in the 9th statement, the 10th roman numeral will be skipped.

This shouldn't be too much of a problem, and the only way I can see to avoid this is to insert an indentifier before the roman numeral.

Hope thats useful