Doing it manually would probably be better, yes, but that's exactly what I'm avoiding since I have about 50 different fields on that single table so creating them automatically saves a whole lot of work.

This is what I came up with, probably not the best solution, but it works:
VB.NET Code:
  1. Private Sub GenericTextBox_Validating(sender As Object, e As System.ComponentModel.CancelEventArgs)
  2.         If sender.Text.Length = 0 Then
  3.             sender.CausesValidation = False
  4.             Dim currentRow As DataRowView = TryCast(EnsaiosBindingSource.Current, DataRowView)
  5.             currentRow.BeginEdit()
  6.             currentRow(sender.DataBindings.Item("Text").BindingMemberInfo.BindingField) = System.DBNull.Value
  7.             currentRow.EndEdit()
  8.             sender.CausesValidation = True
  9.         End If
  10.     End Sub

Thank you for your help Kevin.