I am currently responsible for a fairly large members-only web site that was originally authored in classic ASP years ago and has been partly migrated to .NET. One’s impulse is, of course, to move it to VS 2008 and then go about purging the last of the classic ASP stuff. However, this might be bass-ackwards.
A factor I hadn’t considered is that VS 2003 has built-in support for debugging classic ASP pages, and that this support was removed in VS 2005. So VS 2003 is arguably the place to be if you have a mixed classic / .NET site. You might want to finish porting the legacy pages and then upgrade to the current platform.
It is still possible, however, to debug classic ASP from VS 2005 (and I presume 2008) if you’re willing to manually attach the debugger, but it sounds too much like work to me. You can even cruft up a VS 2005 template so that classic ASP pages show up as a project type and/or file menu item. But you might want to give serious thought to porting the classic ASP pages to ASP.NET before migrating to the current version of Visual Studio. The only downside I can see of doing the port in VS 2003 is if you really, really need to use goodness from CLR 2.0 or later.
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Sounds like something my boss would say. We have a lot of classic asp code and .NET 1.1 code to maintain and no immediate plans to upgrade to .NET 2.0