If it requires more and more heroic efforts to just keep it working, it probably means that your organization can't manage a software project; either because yo

If it requires more and more heroic efforts to just keep it working, it probably means that your organization can't manage a software project; either because your developers are not experienced or, more likely, because management doesn't understand software development (you're not alone; few companies truly master software development). Hence, it's probably not a language problem and switching to Ruby on Rails won't solve it in the long run.