Story so far ...
I tried to get into Win32 development for a long time, but I got my first experience with the Visual Studio 2005 Express editions. The most attractive part of the Express Editions was that they were free. Although advanced features were missing from it, I soon found out the tools provided were quite sufficient for my small requirements. I would rather jump into managed code development with a set of proper and legal tools rather than try out the same with the pirated versions where I had to always remain in fear. There was a version of MSDN for Express Editions too and it provided me with the much needed documentation.
So although I have become a Microsoft Student Partner now and enjoy a MSDN premium subscription that comes with it, the Express Editions still are very near to my heart. I distribute them to my friends and have a copy of it installed on a Virtual PC, in case I need to troubleshoot an application for my friend.
Visual Studio 2008 Express
The newest of the Express Editions is VS 2008 which sports a lot of improvements both in the Windows and the Web development areas. The WPF additions prove to be great. The WPF designer is like a boon for all those people interested in cool GUIs. It is very similar to the forms designer as per using it is concerned. Editing XAML and being able to see it instantly in the split view is cool too.
SQL Server Compact Edition is now a part of the C# and VB Express editions and allows us to create a data-driven application on the client side which can harness the power of SQL Server with much lower resource usage.
Multi targeting is another area that I love. You can target your code for older .NET platforms too, for running on PCs that do not have .NET 3.5 installed. I always use this feature when I do not need any new .NET 3.0 or 3.5 things link LINQ.
Web Developer Express 2008
... and this is what I think
Installing VS 2008 Express Edition over VS 2005 Express is an easy task. Moreover you can continue using it along with VS 2005 too. I currently have both in my virtual PC. Although no major glitches have surfaced so far to shy away for VS 2008, I hold on to VS 2005 just to be on the safe side. You can download Visual Studio 2008 Express free from the official MS sites. There are five different web installs :
and one single Express Edition ISO downloadable for offline installation. I recommend the ISO as you can burn it for later and distribute it too.