It's not possible to use Live Templates to create comment blocks with embedded dollar symbols. For instance, the following comment block uses some CVS keywords to embed version information in the source file:
// File name: $RCSfile$
//
// CVS File: $Source$
This can't be used as part of a Live Template because ReSharper interprets the dollar symbols as its own variable delimiters, and so it mucks up the dollar symbols when the template is added to the code.
Currently there's no way of escaping the dollar symbols (such as using '\$' to mean a dollar symbol that is not part of the Live Template variable system).
$dollar$
In the template to add a variable called "dollar". Choose the macro for this variable and use the "Constant Value" one, then hit "Change Value" and put a $ symbol in as the value. Make sure to untick the "Editable Occurence" box too.