At my company we've been using Typed DataSets for a little while now, and have had a generally positive experience. I understand that many people don't like DataSets, and there are certainly newer data access tools out there, but since you asked about a real-world scenario, here are some of my requirements and findings:
- Need to be able to read SQL Server, MS Access, and FoxPro data sources
- SQL Server access is only through SPROC calls (not my choice)
- Relatively easy to learn, especially to developers new to ASP.NET
I've personally explored low level ado.net access, typed datasets, linq-to-sql, and simply writing custom data access classes. I have not looked at the Entity Framework yet, as the version included in VS2008 seemed to have some mixed reviews, and I did not have access to VS2010 until just recently(I do plan to review EF sometime this year yet).
We chose to use Typed DataSets because they seemed to offer faster development against SPROCS and we found a very comprehensive tutorial by Scott Mitchell on the asp.net site: http://www.asp.net/data-access/tutorials.
As to our experience thus far, it has mostly been good. The DataSet designer generates a huge amount of code even for small number of Tables (<20). Making changes in the SPROCS has caused a few headaches, but I'd like to be shown a tool that would make this easier.
One thing you might try to make your decision easier: Come up with a small domain problem like a customer edit page or order entry page, and implement it multiple times using a variety of technologies. It takes some time to do this, but it is a good way to learn and you can compare the technologies for yourself. We did this and it seemed to help a lot.