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I was researching a little on the philosophy/topic of ".NET DataSets vs. Custom Data Entities" today and came across these two, interesting resources:

Barry Gervin's Software Architecture Perspectives: Datasets vs. Custom Entities

and

"Choosing Data Containers for .NET Series" by Jimmy Nilsson.
Part 1: http://www.informit.com/articles/printerfriendly.asp?p=31099
Part 2: http://www.informit.com/articles/printerfriendly.asp?p=31325
Part 3: http://www.informit.com/articles/printerfriendly.asp?p=31457
Part 4: http://www.informit.com/articles/printerfriendly.asp?p=31672
Part 5: http://www.informit.com/articles/printerfriendly.asp?p=99034