Comment Security may be the best route (Score 1) 379
If the system has an older version of Windows on it, this may be the most tactful way to broach the subject. My experience (15+ years) in freelance tech support tells me that when confronted with the knowledge that an operating system will no longer receive security updates soon (or worse, already doesn't), they are glad to upgrade in order to prevent security holes that might lead to someone stealing their data. This allows you to completely sidestep the issue of possible mismanagement of the old system and start fresh with (hopefully) input from all the board members on how things should go from there.