people operating in contravention of the license agreement .... Which is illegal.
Did you ever read the iTunes / iOS agreement? For a while they had a clause where they own your soul, as a joke, because they knew nobody would ever read it.
Anyway, regardless of licensing agreements, it's a bit daft to run POS2009 because it's not actually XP but XP Embedded which is a bit different and not necessarily 100% compatible, and compatibility is the only reason you should have for running this... making the Vista GUI look like XP is probably much easier.
Running Office 2003 on POS2009 is stupid because although the OS gets security updates, Office doesn't.