I don't know how long ago it was that you upgraded, or that you received help from Sierra's website, but they have sold off the division that did the programming for the Generations software and the only information on their website for Generations is the message boards. There is talk that ?someone? may buy the product line and support it, but nothing I've heard definitely.
If your program does everything you want it to do, and doesn't have any problems working with the latest software and hardware, then by all means stick with it. If you are finding bugs, or wishing you could do something more, you are going to have to look elsewhere.