Migrating from VS2003 and .NET 1.1, at least to VS2005 and .NET 2.0, is worth the cost of signing up. Later versions of the .NET Framework after 2.0 seem to be all additive. It is not or not much to break the .NET class libraries. They just added new namespaces and classes. VS2008 and from what I understand, later versions coming down the pipeline will support backward compatibility with .NET 2.0. This makes it easy to upgrade your IDE (I think you need to convert projects to VS2008 project types), and you get the benefits of new IDE improvements when using older versions of the framework. Some of the larger things that I remember that I only like from the VS2008 IDE are the split view when working in ASP.NET, the new CSS windows and javascript intellisense (VS2008 SP1, I believe in this function).
From personal experience, we had some problems with Active Reports. We had to update versions of this to work with the new IDE / framework, and when we switched from VS2008 to VS2005, some of our SSIS package projects did not open correctly because we are still on SQL Server 2005, so be sure to check all the dependencies which you have. on your IDE 2003 with any third-party applications that you can run.
Ralfondo is right, although I would vote for him if I had a representative. Generics are an alternation of the game, and you do not need to create typed collections yourself to have type safety. Seriously .... google search, what should you do in .NET 1.1 and later. The difference is night and day.
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