Hi, I've done some research on your project, and here are some of my thoughts:
1. According to Oracle's documentation, using AWT/Swing, I can create SystemTray menu for both Windows and Mac OS X.
2. As of copying text to system clipboard, I can use AWT as well, and it gives me Clipboard, and Clipboard owner, where I can read and write data.
3. When paste delimiter is set to 1, I can paste current clipboard conent with AWT Robot, by simulating a Ctrl-v command to the current focused window.
4. TCP/IP communication is definitely workable.
So, if you allow me to use AWT/Swing, I'm confident to finish your task in time.
And for a self-intro, I'm a seasoned Android and iOS developer who also build Mac OS X apps. Here's two of my apps:
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And I'm looking forward to work with your project.