Every year for the last 7 years a couple of my cousins have rented a cabin near the Alleghany National Forrest in on the border of western NY and PA.
They have a big trailer that they pack up with everything we need for the week, and they show up with their HD and Honda 750/4, and I ride out with my VStar 650. At most I bring a few changes of clothes, personal items like meds, toothbrush...
I think that is the best way to go, someone else drives a Ford 250 pickup towing the group trailer, and we get to ride our motorcycles there and back, and all around the forests with no baggage or trailers on our bikes for the week.
I understand the desire for independence, to be able to go your own way at your own pace, and carry/tow everything you need with your motorcycle, but it really takes away from the joy of riding an unloaded bike.
If you can get together with a small group of riders, have one person or couple switch off and drive the chase vehicle each day, with all the luggage, and then everyone gets to ride their motorcycles unencumbered.