On the MCB2140 board the USB HID example runs fine, in order to understand code flow, I enabled UART0 to be my debug port. When I attempt to DebugOut text during USB transactions, my DebugOut routine gets one character out then freezes. I've tried switching the priority using VicVectCntl with no success. Any ideas appreciated.
You've inserted the DebugOut to USB ISR. Unless nested interrupts are enabled, you can't expect any other interrupt, regardless of priority, while an ISR is running.
Also, sound like your DebugOut blocks the target process until full texts have gone out. It'll cause timeout error on USB enumeration on the host side.
Rewrite your DebugOut routine, so that it doesn't block the target process so much. For example, the DebugOut puts the debug strings to a ring buffer. Another process puts the text on the buffer into UART.
Tsuneo