First off, to answer the original question, I think you should be able to get those four sleds into that trailer. I had a 22 and never got 4 in that, but several guys on this board talked about how they did it. With 3 short ones you should be able to do it in 24.
Now, I agree with everyone else, there is no way I'd pull that trailer loaded with a Pilot. I had a Sport Track and while it was rated for over 5,000 I upgraded to a 1/2 ton Silverado to put my 7X22 inline. Fully loaded it was only 3,700 but the wheelbase on the suv is way to short and I wouldn't want to get pushed around on the snow packed UP road, especially heading down Military Hill on my way up at the start my trip, usually sometime around midnight. Getting pushed into the ditch, or worse yet, the river, would not be a good way to start a trip.