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CodeSmith Generator ships with a sample project, CodeSmith.CustomProperties, that includes some useful property types for your templates:

FileNameEditor can be used to let the user select a filename as the value for a property
StringCollection can be used to let the user enter a collection of strings as the value for a property

You can find this project in your extracted samples folder (Documents\CodeSmith Generator\Samples\<VERSION>\Projects\CSharp\CustomPropertiesSample).