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Depending on how much muscle that you can muster for help---
First look at (and measure) the height of the rear bumper on your tow vehicle to the ground.(Check the "tongue weight" of your tow vehicle in your vehicle owner's manual.
Once your trailer is fully loaded, you want the trailer to sit a little lower in the front than it does in the rear and you want the majority of the load OVER the trailer axles but you don't want to EXCEED the "tongue weight" of your tow vehicle.
If your trailer sits much higher in the front than it does in the rear, you may want to get another (more drop) ball insert that may lower the front of your trailer, which will make it much easier control.
Be sure that your trailer tires are fully inflated and check them frequently as underinflated tires will overheat faster than those that are properly inflated.
I'd suggest that you try loading the heaviest bikes on the trailer first and then "slide" the rear wheels of these bikes as close to the outside edge of the trailer floor as possible.
Then place the Tri-Glide in the center of the trailer, as far forward and between the two bikes as possible.
Once this is done, see if you can then maneuver the lighter bike
onto the trailer behind the Tri-Glide
Followed by the next heaviest and then the lightest, leaving the last part of the trailer open for the 1200 lb. Tri-Glide, IF enough room is available.
Good luck!
I have an 8'x20' heavy duty landscape trailer that is set up for 4 H-D's and there may come a time when I'll be pulling 1 Heritage and 2 Tri-Glides, so let us know how this works out.
Don't know if this helps, but 3 years ago I hauled 2 baggers in the front and the other guys wife's freewheeler and my wife's tri glide in a 20 ft. enclosed. Put the 2 baggers up front then the freewheeler pulled in and the tri glide backed in from Pa to MB. Used lots of straps All other bikes we're pulled in, except the tri glide Was a little tight with the trikes but was doable
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