Even though I gassed onandonandon about the trailer, I side with those suggesting you ride it.
Will you make mistakes? Yup, we all do. The biggest mistake I made was letting 41 years elapse between my first long bike ride and my second.
Go for it.
When I set out on my second trip, I was 64 years old, and I had the crazy notion I could ride 400 miles per day ... eight days in a row! I left Toronto Canada at noon on a Sunday, expecting to reach Vancouver BC late the following Sunday.
I hoped I would reach Chicago on Tuesday. I reckoned I would know whether I wanted to keep riding, rent a van and haul the bike with me, or shove the horrid thing into Lake Michigan.
Well, lemme tell you, the miles rolled on and on, and I did NOT reach Chicago on Tuesday. I did not reach Chicago on Monday. I passed Chicago the same Sunday I set out. I took six days for the ride, including a side trip to Denver CO, and got there Friday evening. The ride back east took five days.
Budget five or six days for this ride, and you will enjoy it a lot. You can get a campsite for under $25 per night, but in those wide open spaces, there are probably lots of places to pitch a tent for $0.
A show of hands, for people who would want to ride with you, would probably amaze you. Here is mine:
As I said, courage!