Why in the word would you want to bring a trailer inside your tent? Trailers get dirty. Trailers get muddy. Trailers take up space. A B.O.B. trailer has metal edges that can damage tents and mattresses.

Have you done one mile of touring? If not, I suggest you give it a try, or at least load up that trailer and dry bag with a bunch of weight and go ride some hilly terrain. You will get a better idea of what the experiience is like and what you aere capable of than you will asking others on BF.