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Hi, welcome to the forum! Writing a plugin is indeed realistic if you're familiar with c or better, c++, and are determined enough to put in the time and effort to see your project through. Others may not agree, but I found the most straightforward way to write plugins is with Hot Door's CORE platform (HotDoorCORE.com ). If you have Xcode or Visual Studio 2015, I'd recommend downloading it and try compiling and modifying some of the example projects. Best of luck!
Which version of Illustrator was the last supported by the plugin? What does the plugin do? Have you tried contacting the developers to see if they could be persuaded to create a CC version or to sell you the source code?
Yes, it is possible to write your own plugin, but I don't think it is realistic for you to be able to replicate a plugin that was sold for $400. For that price I would assume that it includes functionality that is not in the public domain and is difficult to replicate.
Challenge officially accepted. How would I go about finding out how the plugin was created? Might it be best, since I'll have to be able to recognize what it's doing, to learn the software that it's been created in? I can't remember the last Visual Studio I used, it was like a decade or probably more ago, and I'm probably ridiculously rusty in C++, but I'd still like to try. I'll definitely be checking out that hot door core.
It's software that adds lines and marks for helping with finishing in printing. The price is high because the crowd of buyers is small. It doesn't do anything remarkably complex, an example is that it adds evenly distributed marks along the sides of document pages, with a handful of variable like bells and whistles, Printing on two sides of things has a few snags when folding over the edges, the left side flap needs to match the right side of the second side. Sometimes rotating or mirroring and moving edges of pdf pages, so the 'fold' matches the other sides. It's all very well done too, all professional. Some of the actions it does, such as making multiple copies of larger embedded artwork, and splitting those up and assigning them to new locations, and... unusually fast. Seemingly much faster than using commands in Illustrator could do.
It runs on a computer with CS5, but won't work with CC, I'm not sure why yet. We've tried contacting the developers to pay for an updated or upgraded version, and were told that it's no longer an option. I believe as well, that we even offered to buy rights to it, and that was also declined.
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You will need to learn how to use the Illustrator SDK, which is used by all plugins, or as Rick suggested use an SDK wrapper library.
The plugin won't work with CC because it was compiled using a CS5 compatible version of the SDK which is not compatible with CC.
If that is all the plugin does, it sounds a bit overpriced. If you only want the basic functionality of the plugin and are not bothered about a fancy GUI, you may be able to achieve what you want using Illustrator scripting or even actions.