We have an application that was originally installed in 1998 on version 8.2.  The application was upgraded in 2005 but against the old 8.2 database version.  The application is now at end of life and will cease to be supported in 2013.  Since the app runs, the business unit really has no stomach or reason to want to do much of anything.  However, from an IT standpoint, I'm looking for options.  One option I'm trying to evaluate is to at least upgrade the database from 8.2 to 10.x.  
Is there a direct upgrade path - or is that a fairly complex task? Also, would a progress app that has both windows and dos windows components from 2005 even run with an upgraded database back end - or would everything just quit working?  (I know these are generalities - I'm trying to gauge risk to help the business unit in making a decision on purchasing new software or risking this system to keep on running.)

Any advice would be greatly appreciated.  I'm more of a SQLServer/VB/C# person and know almost nothing about progress other than how to install the sw, compile a module, and start/stop the services.
Thanks