I decided to do the following approach.  If anyone has a better solution let me know.  Thanks!
In my hibernate mappng file I created a new property..
Code:
<property name="DaysCheckedOut" formula="DateDiff(dd,CheckedOutOn,getdate())" />
Using the DetachedCriteria now yields a statement like..
Code:
detachedCriteria.Add(new NHibernate.Expression.GtExpression("DaysCheckedOut", 50));
The only problem with my approach is I really only need the DaysCheckedOut property when a user filters by this field.  Since I made it a class property it will now always be part of the query when retrieving data.  Not a huge performance penalty but I'd rather not always pull the field.
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