AutoIt is not only a great language to automate any MS Windows based tasks, but also has the best Help file I have EVER seen for any language or framework out there. Then you add the forums on top of that. The forums are a great resource to search through, and also to ask your questions!

I have created an entire testing framework for a previous employer completely written in AutoIt. It allowed them to easily create new test cases without writing any code, and then it allowed them to schedule the test cases to be automatically executed. AutoIt is a very flexible language, and is quick and easy to pick up and learn. I would recommend it over VB or VB.NET as those have a higher learning curve, and I don't feel they can do the same job with the same ease that AutoIt provides.

AutoIt allows you to create simple scripts, or complex GUI Applications. It's your choice. It compiles into a single executable. You can even include files into your executable to be unpacked at runtime to be used. There are so many unique features. A simple AutoIt script is also a little over ~200kb. That's all the overhead. As your script gets more complex that grows, but not significantly. (Unless you add files like I was saying). AutoIt was originally designed to automate tasks across the network, and it needed to be small enough to be able to be sent all over the network without clogging the "pipes". That vision has continued to be maintained.

I wanted to address what someone said above about upgrading to the latest and having some issues with the functions they were using previously. AutoIt is very good at marking changes that have occurred, and they try to not implement things that break previous versions, but as with any living language things do change, and before you upgrade to the latest framework of anything you should always test it first. I understand the frustration...(I had multiple scripts to update as well)...but all that had to be done was a bit of research, and then things would have been much easier.

AutoIt
AutoIt Forums
AutoIt Documentation
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I hope this helps you in your endeavor,
Jarvis

I would also highly recommend TaskCoach. It's under constant development, as well as it's cross-platform so you can keep track of your tasks no matter what machine you're on.

I believe it also covers the entire range of features you're looking for in a task tracking program. It's certainly one of the best I have seen thus far! Very customizable as well so it fits YOUR needs!

I would highly recommend having your child learn a high level language. One that I really enjoyed learning more on when I got started was AutoIt. Unfortunately it's only for Windows. Also web programming is a lot of fun and provides quick returns for minimal investment. If after they still are showing interest in programming, then they can then spend a bit more time and learn a few lower level languages.