Where to start ?

The first big challenges when doing a project like this are,

what language do I know that will give me the most flexibility while not forcing me to do redundant scripting?
It’s true that this project could be done in many languages, could even be done in AutoIT but that would make for a very long redundant project.
AutoIT is great for macro building but doesn’t suite our need for flexibility of windows forms. So I need a language that I’m very familiar and that will give me the flexible window forms.

I went with VB.net, while I’m familiar with C++ I haven’t done enough of it to make it a feasible choose.

Keeping organized,
This in itself can be a huge problem down the road, not just organization but leave yourself some footnotes to look back on.

I solved this by making several modules to handle different functions like “CompFunc” holds all my computer functions like getting regristry information, reading and writing text files. Or my “Curse” module that holds everything curse related.

Resources,
If your not sure what you need to use to do what your looking for need to have a place to look it up.

Google is your friend =)