A little late with a response but first off, many many thanks for your service! Some things to consider with the towing set up for your bike is the rear tire and chain and sproket wear. I see you have a Harley and they use a belt drive but would have the same considerations. Second you can't see it. What if the rear tire blows on the bike? That could get ugly real quick. Can't back up. That could be a real problem on longer trips. Years ago I used one to get a Yamaha 650 back and forth to school...It was nerve wracking and I could see the bike in the mirror. My suggestion is a good set of ramps to put the bike in the truck and a headache rack for your truck for the sufboard etc....
Good luck and thanks again!