MisterC,
Thanks again for the great advice and I will let you know how it all works out. I'm certain the issue is your #1 Possibility
1. The previous homeowner's Lutron rep configured the IP as static, and your network is now configured with a different network range.
I hear you loud and clear when you say "It's likely one reason why Lutron doesn't want homeowners doing this form of support, and relies on technically knowledgeable reps."
When I explained my situation to the Networking Team they all looked at me like I had two heads and said with all the much more user friendly options out there for controlling lights why are you using Lutron. I explained, I'm playing the cards that were dealt to me.
All I'm trying to do is update the firmware on the main repeater, that's it. Shouldn't I as the home owner at least be able to do that without having to call in a Lutron Tech, I'm not asking for the keys to the kingdom. I know how to upgrade the Firmware on every other device in my house so why not the Lutron main repeater.
I'm not trying to sound ungrateful for all of your great advice, because I do truly appreciate all of it, I would just like to be ale to do a little for myself.
Thanks again for all of your great advice and I will let you how it all turns out.