I have had this same problem and the conclusion I came too after scouring the web and reading other user's stories is that VS 2008 has a bug when debugging classic asp! It crashes when you stop debugging. Sort of a time killer to have to restart VS every time you debug.
I have had to resort to using VS2005 to open classic ASP projects and debug them there. If I need to have the ability to work on an app in both 2005 and 2008 I've found that you can have 2 separate solution files, each created by the applicable app (for example I've got appName.sln that I open in VS2008 and then appName2005.sln that I open in VS2005). You will need to create a new solution in VS2005 and add the files, then save that solution with the slightly different .sln filename. This works, it just takes a bit of time to setup.
Supposedly MS is going to resolve this issue in VS2010 but they didn't consider it an important enough problem to issue a patch for VS2008.