I\'m creating a UserControl I want to use something like this:
I know this has been answered but none of the explanations give an Understanding of DataContext and how it works. This link does a great job for that.
EVERYTHING YOU WANTED TO KNOW ABOUT DATABINDING IN WPF, SILVERLIGHT AND WP7 (PART TWO)
In answer to your question #1
Why doesn't work?
This is a summary of the above link. DataContext should not be set to Self at UserControl Element level. This is because it breaks the Inheritance of the DataContext. If you do set it to self and you place this control on a Window or another control, it will not inherit the Windows DataContext.
DataContext is inherited to all lower Elements of the XAML and to all the XAML of UserControls unless it is overwritten somewhere. By setting the UserControl DataContext to itself, this overwrites the DataContext and breaks Inheritance. Instead, nest it one Element deep in the XAML, in your case, the StackPanel. Put the DataContext binding here and bind it to the UserControl. This preserves the Inheritance.
See also this link below for a detailed explanation of this.
A SIMPLE PATTERN FOR CREATING RE-USEABLE USERCONTROLS IN WPF / SILVERLIGHT
In answer to your question #2
What is the best way to do something like this?
See code example below.
Note that once you do this, you will not need the ElementName on each binding.