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I've submitted this a bug report to oracle, I'll be contacted within the next couple of days if it is a valid report. I got someone else to execute the code above and it does hang for them as well.
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Alright, I've managed to recreate it in an isolated environment (the code looks like complete nonsense since it's just a bunch of unrolled loops with the area operations isolated):

*EDIT*
I have...

Alright, I'll see if I can figure out what sort of data is being fed to these objects is causing the main thread to enter the loop and try and recreate it in a small bit of code.

For what its...

I have run my code through a profiler and also used the following debugging technique to infer that this main thread in my application is being locked up due to a call to Area.Subtract (Also...