Obsession 2 software fun

I just started working at a Road House with an O 2 1500 Single Processor. Sadly it hasn't been updated since it came out of the box, leaving it running on V 4.4.2.  Thus far my attempts at an update have met the sad sounds of a console operating under the thumb of Windows 95, and not wanting to play nice with my updates from any software out of the new millenium. Do I need to find a sacrificial computer to convert to a more seasoned operating system, or am I just missing something painfully silly (equivalent to not having the master up?)  Any advice or assistance would be greatly appreciated.

Thanks,

 

Zack

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