Re #2: We took a 3 1/2 month trip in 1998, pulling a travel trailer, going from Chattanooga to California to the eastern end of the Alaska Highway to Alaska, on the ferries back to Vancouver Island, across the northern tier of states, and back home. We drove over 16,000 miles. The first leg to California was pretty much structured, but after that, it was free-form except for having to deal with ferry reservations toward the end.
We also went cross-country in 2003, mostly following the Lewis and Clark trail, then coming back on a more southerly route - also with the travel trailer - again, with no set itinerary.
Way too much information to get into at one time, but I'll chime in from time to time, and will be happy to answer any questions. We did the first trip after having the trailer for only a couple of months and taking two weekend trips locally. We had no problems - I guess sometimes good fortune looks out for idiots.