Except that we are an all-Microsoft shop with no Java expertise on staff (except me, and mine is dated). Java would have been a better solution for the original ASP application, but I can't see it being an improvement over the ASP.NET version.
Well, it would have been more scalable and fault-tolerant, for sure.
ASP, even ASP.NET, doesn't scale very well.
You wouldn't have "single-vendor" lockin for your DB or web server -- there are far better web servers out there than IIS. If a more complex rich-client Gui was required, you'd be able to scale to a Java applet.
It would be less risky, since the Java has been heavily tested in real work for many years and the .NET version is brand-new, and certain to have many issues pop up.
And if you had done it in Java to begin with, you wouldn't have to have revisited the issue later, like you did.
It sounds like since you're an MS-only shop, they paid you to use the lesser technology even tho a better solution was available. You were forced to use the lesser technology. I'd say that's still the case with your locking to IIS and SQLServer.
You know, there is no such thing as a "Java-only" shop like there are MS-only shops.
You have 2 kinds of software shops -- ones that use the best solution available, regardless of tech (and they all use a mix of techs, with Java doing most of the heavy lifting) and then the shops who are 'MS Strategic Partners' and 'MS Early Adopters'. They're paid to use MS-only.
If MS is having to *pay* companies to *force* use of their technology, that is not a good sign for the technology's future.