i have a 16 foot dovetail. you will fit with the box blade up front and the tractor pulled on foward and not be hanging off the trailer, I put my 12 disk double gang harrow backwards all the way to the front of the trailer and back my tractor on with bushhog up and then set it down on the harrow and the front tires are like 18-inches from the end of the trailer. Strap the harrow down the bushog down to keep from flopping and strap the tractor to the trailer across middle and on the front bumper it all fits. You may be able to drop the box blade then the tiller up front and still be able to pull on the trailer foward with little hang off or back on with the bushhog on top of the other impliments, that would work. The other way if trailer is wide enough is to pull tractor on foward just enough to get the tail wheel on the trailer and put the BB and tiller , one on each side of the tractor on long ways, or sideways and strap them on either side of the front tires, not sure if a standard trailer is wide enough for this but i have a 2000 and the 1500 is smaller? Oh and all this is without the loader, that you will need at least 18 ft for.