The asp.net solution would be more elegant and easier to deploy and update, but it is really more of a judgment call. There is twice as much to manage when you have two exe's though...

The asp.net thing isn't too hard to pick up. My suggestion is to pick up a asp.net book and read the first 4 chapters at the very least. Should only take two days. This will at least give you a basic understanding of the technology so you can start building with it. It is still VB.Net or C# code, so that isn't a problem.

Also, for datagrid controls, the "ASP.Net Data Controls Kick Start" book is awesome. Might want to look at it.

Good luck.