Depending on the type of diagrams you make, a reordering icon is displayed on the modeling toolbar in the toolbar. Alternatively, right-click on the background of the chart to find and select this option. However, I'm not sure that you will be satisfied with the result of VS2010 auto-linking capabilities.
For example, in a sequence diagram, click the layout icon to the left of Create Work Item : 
(this is not available in the class diagram)
Only the VS2010 Ultimate version allows you to simulate projects, so it answers the second part of your question.
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