I have decided that Ruby on Rails is the best toolkit for what I need right now. So, what I am going to do is take the time to learn Ruby and then start familiarizing myself with Rails. I can build the foundation on Windows without any problem because Ruby is well-supported on Windows and the Webrick web server that Rails provides should be good enough for testing the application.

For the database I plan to use SQLite because that should be the easiest thing for most people to safely have on their system. I could use ASP.NET and Access, but that would require that users install IIS and that would end up causing a lot of problems in its own right. So, I think that a pure open source approach to this will end up being the best.