Okay I have been testing some stuff and I have found that the actual problem with the crashing is DB not recognizing the plugins folder.
The first time I load DB it "works" fine until I try and actually start the bot. It appears DB is not reading from the plugins/routine folders. So when I try and select a combat routine ex Trinity DB can't find the folder and throws an exception that I am going to venture a guess was not handled by DB's code and it crashes. Now from here every time I attempt to start DB it looks for the combat routine that it couldn't find before and immediately crashes.
Now, I don't have the source code to DB, but if you write a unit test around selecting the combat routine and pass a null value, I am going to go out on a limb and say you will see what I am seeing.
2014-09-25 13:23:21,170 [1] INFO MainWindow (null) - Demonbuddy v1.1.2135.382 started
2014-09-25 13:23:24,136 [5] INFO MainWindow (null) - Logging in...
2014-09-25 13:23:24,728 [5] INFO MainWindow (null) - T: 5247158500469324990 H: 3325093573
2014-09-25 13:23:24,978 [1] INFO MainWindow (null) - Attached to Diablo III with pid: 3988
2014-09-25 13:23:24,988 [1] INFO MainWindow (null) - Flashing window
2014-09-25 13:23:25,903 [1] DEBUG MainWindow (null) - Executable Path: C:\Users\Robert\Documents\Demonbuddy\Demonbuddy.exe
2014-09-25 13:23:25,903 [1] DEBUG MainWindow (null) - OS Architecture: AMD64
2014-09-25 13:23:25,903 [1] DEBUG MainWindow (null) - OS: Windows 8 64-bit
2014-09-25 13:23:25,908 [1] DEBUG MainWindow (null) - OS Language: English (United States)
2014-09-25 13:23:27,078 [1] INFO BotMain (null) - Current bot set to Order Bot
2014-09-25 13:23:27,083 [1] INFO ProfileManager (null) - Loaded profile Rift Bot Loader
2014-09-25 13:23:56,255 [3] INFO ZetaDia (null) - Diablo III Exited, Demonbuddy terminating in 20 seconds.
I was comparing a good session vs what I am seeing now and it appears that DB no longer recognizes my Plugin folder.
2014-09-01 02:32:31,415 [1] INFO Logger (null) - [Armory] v1.2.12 Initialized
2014-09-01 02:32:31,417 [1] INFO Plugin (null) - [GearSwap] 2.2 Initialized
2014-09-01 02:32:31,425 [1] INFO X+Logger (null) - Registering Gamble behavior for BotBehavior Hook
2014-09-01 02:32:31,427 [1] INFO X+Logger (null) - Registering Gamble behavior for VendorRun Hook
2014-09-01 02:32:31,428 [1] INFO X+Logger (null) - Gamble Initialized!
2014-09-01 02:32:31,431 [1] INFO X+Logger (null) - Registering Townrun behavior for BotBehavior Hook
2014-09-01 02:32:31,431 [1] INFO X+Logger (null) - Townrun Initialized!
2014-09-01 02:32:31,434 [1] INFO Logger (null) - [Trinity] Initialized v2.0.1
2014-09-01 02:32:31,921 [1] INFO Logger (null) - [Armory] v1.2.12 Enabled
2014-09-01 02:32:31,930 [1] INFO Logger (null) - [EZUpdater] Enabled
2014-09-01 02:32:31,932 [1] INFO Logger (null) - [EZUpdater] Starting EZUpdater Thread
2014-09-01 02:32:31,934 [1] INFO LumberJack (null) - [LumberJack] Plugin v1.0.19 Enabled
2014-09-01 02:32:31,937 [1] INFO Logger (null) - [Plugin] v2.0.91 Enabled
2014-09-01 02:32:31,951 [1] INFO Logger (null) - [Trinity] OnEnable start
2014-09-01 02:32:31,957 [1] INFO Logger (null) - Setting up Trinity Logging
I don't know if any of this helps you solve my problem or if its even useful, but thanks for your time.