 <p>Strongly opinionated answer ahead:</p> <p>I have tried a few different approaches to binding in WinForms (over many years), and it ends up being really easy to get 80% of what you want, and it requires significant hacking to make the other 20% work. Also, usually 3rd party controls come with their own quirks.</p> <p>Your list there illustrates the pitfalls fairly well. Unfortunately, WinForms just doesn't have the binding power of, say, WPF.</p> <p>My current approach to data binding is to do not use any of the binding objects and do everything manually. The approach I usually take is just make the form a <a href="http://coding.infoconex.com/post/2010/01/16/%28MVP%29-Model-View-Presenter-Passive-View.aspx" rel="nofollow">passive view</a> and pass the Form a ViewModel object encapsulating all the data that should be displayed on the form and set all the properties on the form from that object. Which means you lose all the 'magic' of binding, but it's not a black box anymore and it's easier to debug.</p> <p>Good question, I look forward to other answers and being proved wrong.</p>