Advice on creating a Plugin/script

I wasn't really sure where to put this. None of the forums seemed to fit this so I just stuck it here. If you'd like it better somewhere else, please move it there :P

Anyways, I'm looking at the possibility of creating a custom plug in/script for Acrobat to speed up what I'm doing at work(and to also give me something to write my work term report about...because this is without a doubt a first year job and there's not much for me to write about :P). I wanted to get some advice on whether what I want to do is possible to make in Acrobat and if it would be feasible for me to get something up and running before the middle of August.

I want to create a plugin that gives me a new toolbar button. When the button is activated, I want to prompt the user for a number to start counting from. After that number is entered, each time the user clicks on the screen, I want a circle of a constant size to be drawn where they clicked and the circle numbered inside it, starting with the number entered. The number should increment with each click. When the button is deactivated, everything goes back to normal.

I have not worked with Acrobat at all before in terms of custom features so I don't know whether this would be more suitable as a plug in or as a script. I do have some programming experience. However, it was just a first year general engineering programming course(which unfortunately has been dumbed down from previous years...). It was just procedural programming in C++ and was limited to only console applications, mostly which involved basic file I/O and making algorithms to solve for random things. We also made super awesome lego robots do stuff with RobotC. We didn't cover anything to do with classes and data structures, so my knowledge is fairly limited in terms of C++ and programming in general. I'm definitely willing to learn though and picked up what we were doing in class much more quickly than my peers, despite having no prior experience.

I guess what I'm asking is:
1) Is what I want to do possible in Acrobat via a plug in or script(and if so, which would be better suited)? If it's not, what other programs would you suggest?(It's currently being done using Microsoft Visio...but the circle drawing and numbering steps are separate, which takes a ton of time, the file sizes are huge and Visio has been butchering the image quality so that's why I'm looking at other options..)
2) If it is possible, is it realistic for me to pick up the knowledge that I'd need to know and be able to create + debug the plug-in/script by about mid August(I need some time after it's done to write a report up etc.)? I would be only be able to work on this in my spare time and possibly if I had nothing else to do at work.
3) Are there any good references for learning the necessary concepts and moving over to OOP that you'd recommend? I've found a couple of references straight from Adobe, but I'm having a difficult time finding ones from version 9(Is there anything major that changed? Or would versions 7 and 8 probably be sufficient?)
4) What sort of compiler/editor would I need to use?