In the long run the joy of riding the TW as you plan to will likely overshadow any memories of the purchase price pain. Cannot speak to what should be reasonable Illinois dealer prices. However as riding season is coming to a close perhaps with patience a good used deal may be found.
These bikes can hold up well over countless thousands of miles. It is a personal decision as to whether saving a thousand dollars or so on a used bike with untold thousands of miles is a good deal or not. Often some of the purchase price savings goes back into replacing aged or worn items like tires.
Certainly the convenience of a dual sport’s ability to go from public roads to goat trails is a game changer for enjoying Colorado and Utah’s backcountry.
Good luck on a good plan and a big welcome.