How do you decode and view the actions of software(i.e. VoIP program) to write a program that can interact with it?

mr_wizard

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For the purpose of my question we'll use "Skype" on Windows XP, for example. Say I want to have a program that runs with the ability to monitor, recognize an incoming call (or any state of any VoIP program or otherwise), answer it, and maybe even possibly play a .wav file that the caller hears. I have an A+ certification, have been working on a tier 3 desktop engineering role for several years, understand network topology, active directory of course, html code, and am "very" fluent with writing batch files. I draw the line not far after variables. With that being said, with someone that has pretty severe ADHD and hates Math, what approach would you recommend? I've dabbled with WScript before, tried C++ (failed miserably), and have a very loose understanding of vbscript. I've been convincing myself for awhile it's time to graduate from prompt and learn a language with potential for things like this, but one that I can actually grasp. From what I'm reading and comprehending, "Python" is the language of choice for this. Which at first glance looks like a rats nest without the focus of a coke addict. I will however, give it a shot, if I can get confident answers. I just don't want to invest time into an attempt only to "fail miserably" again on something that wasn't recommended for the right reasons, or by those who understand my situation. However, given my background, what would you folks suggest?
 
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