Your biggest issue is that your technology is already out of date. For example Prinergy and Insite runs on Windows 2003 Server and Microsoft has already ended support for that OS. And you can't run it on any newer version of Windows Server. And I know Workshop for Prinergy 5 won't install on probably any OS X version after probably something like OS X 10.7 or 10.8. And as web browsers are updated you're going to find more and more of them are going to block both Java and Flash. Both of which are used heavily in the old versions of Insite. So while you may be able to keep it running it will eventually not do you any good to do so.