WrenchJeff,
Welcome!
For service contracts (Chrysler), go here -
www.chryslerservicecontracts.com
I'd recommend purchasing the highest one you can - as fixing just a few small things will pay for itself.
The keys can be bought on Ebay, you can program it yourself after having it cut.
The books can also be found on ebay.
The NAV CD's can be downloaded/burned off of this site - a little complicated, but it can definitely be done.
Do you ever make it further south in TX? Ever in San Antonio? We have meets quite frequently and would be glad to have ya.
Take care,
SQ