That is a lot of trailer for a 2500. Make sure your payload ratings are high enough for that pin weight and GCWR is good for the total weight.
As for the route, I definitely would not recommend US 550 from Silverton to Ouray
(the million dollar highway) on the way to Grand Junction. That is a very steep winding narrow highway with no shoulders going over three high mountain passes. Especially so for someone towing a 5er for the first time.
And secondly the amount of time. From Hunt direct to Yellowstone and back alone is at least 6 days long days (probably in excess of 10 hrs per day) of travel without even considering all the other places you mention. Even on the interstates, with stops for rest/food/fuel you probably will not average much better than 55 miles per hour if that much. Add in all the side trips and you would probably be on the road 10 days or more. Not much time to actually stop and see things. That trip will be a killer for all.