Hi & welcome to the board.
How about
Private Sub Worksheet_Change(ByVal Target As Range)
  If Target.Address(0, 0) = "V17" Then
    If Target.CountLarge > 1 Then Exit Sub
    If Target.Value = "" Then Exit Sub
    Select Case LCase(Target.Value)
      Case "prosurance"
        ActiveSheet.DrawingObjects("CheckBox1").Value = True
        ActiveSheet.DrawingObjects("CheckBox2").Value = True
        ActiveSheet.DrawingObjects("CheckBox3").Value = True
      Case "care"
        ActiveSheet.DrawingObjects("CheckBox1").Value = True
        ActiveSheet.DrawingObjects("CheckBox2").Value = False
        ActiveSheet.DrawingObjects("CheckBox3").Value = False
      Case "mi only"
        ActiveSheet.DrawingObjects("CheckBox1").Value = False
        ActiveSheet.DrawingObjects("CheckBox2").Value = False
        ActiveSheet.DrawingObjects("CheckBox3").Value = False
      Case "assurance"
        ActiveSheet.DrawingObjects("CheckBox1").Value = True
        ActiveSheet.DrawingObjects("CheckBox2").Value = True
        ActiveSheet.DrawingObjects("CheckBox3").Value = True
      Case "pm only"
        ActiveSheet.DrawingObjects("CheckBox1").Value = False
        ActiveSheet.DrawingObjects("CheckBox2").Value = False
        ActiveSheet.DrawingObjects("CheckBox3").Value = False
    End Select
  End If
End Sub