I had a quick look at your code and i can't see anything in there that looks wrong. And it works ok for some times before the problems start.
So right now i have two "suspects" memory fragmentation caused by GoBetwino repeatedly opening large files, (even more suspicious now when you mention multiple log files), and the other suspect is the status and command output textboxes that will grow very large with your usage pattern. Maybe so large that it becomes a problem for Windows (there is a limit to the amount of text a textbox can contain)
The problem with memory fragmentation is that it is difficult to avoid
I will try to make an Arduino sketch that mimics your usage pattern and see how it runs here.
What version of Windows are you running ?