As I began writing web applications with ASP.NET I started with small projects that used a Linq-To-SQL mapper for database access to a MSSQL Server.
After gaining some experience, I switched into a classic three-tiered approach with a graphic Layer, business Layer, and a data Layer. The only function of the data layer was to provide insert/update/delete-methods without any logic and logic the form of selection methods.
Over the time I realized that it would be better not to provide the database classes up to the GUI (took some time, unfortunately). I switched to using business classes in the BL that are used for all operations performed by the BL and displayed by the GUI in the form of getting List from the business layer.
A great advantage is that I can provide additional properties that are not represented by the database itself. However, I did that mapping inside the business layer myself with methods that mapped the corresponding business layer class to the database class.
I guess that's where O/R mapper come in handy? Until now, I haven't realized their purpose, but I think I just found it. I've recently tried out using the new Entity Framework with .NET Framework 4, but I'm only using it like the Linq-To-SQL DataContext.
Is there a way to achieve the mapping automatically? If yes, is that something the new Entity Framework provides or do I need to look for a O/R Mapper like NHibernate?
LinqToSql is an ORM, so you are already using one. Taking LinqToSql out and replacing it with EntityFramework or NHibernate won't solve the problems you appear to be having right now.
Here are some things you should learn more about to help give you additional context: