I just hauled a CB750 back from Florida last weekend. F150 crew cab with a 6’ bed so yes, had to run with the tailgate down. Of course, your looking at about 535 pounds so a big difference. The best part was the loading and unloading. Seller had a HF lift so we just pulled that thing into the driveway, lifted the bike, and pushed her in. Got home, backed into garage, and unloaded with my lift. Hey maybe that’s your answer. Carry one of those $279 lifts with you.
There was a longer thread on this subject sometime back. The general consensus was it's a bad idea, however to each there own as I've happily ran with some sketchy loads in my truck before. My issue would be the 1/2 ton short bed truck. The bike alone puts you a near capacity and then your adding a trailer to it. Bike or trailer by themselves and you'd probably be alright but together I'd think you'll be asking for some type of mechanical/structural failure. You'll do what you need to make it work, however it may require some truck upgrades to do safely. Keep that in mind and with some thought an planning you should be okay.
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