Yes, that's a definite problem.

One thing we very much like having at Pennsic is a goat-wagon that holds a lot of musical instruments in their cases. But we had pulled that out of the trailer some time in the past three years to carry one or another elderly dog to the park, which they still liked very much but no longer had the stamina to walk to. Since then, the goat-wagon has been in one side of the garage, the trailer in the other side, and an ever-increasing accumulation of stuff in between. So to get the goat-wagon back into the trailer, I emptied a bunch of stuff out of the trailer and pulled it out of the garage by hand onto the sidewalk. Then, since it was already out there and accessible, I packed not only the goat-wagon but a bunch of furniture and tentage into it. Which of course made it too heavy to move by hand, so I hitched it to the car just long enough to get it back into the garage for the night. Today, we throw a few more things into the trailer, put foodstuffs and instruments into the car, and head out. Or that's the theory.