I have the Truck Covers USA aluminum retractable. It is spring loaded so when open it is snug against the box. No problems there, I haul with it open all the time. It also has locking position about a foot apart. Expensive but really nice product.

 

I have a retrax on my '05 F-150 Super Crew. I am able to haul my Grizzly 660 with the Retrax but I back it up into the bed, and the front tires rest on the open tailgate. I also built a wooden frame that I put against the back of the bed that prevents the ATV from hitting my Retrax. I have the bed extender that I use to ensure the ATV stays put.

 

For your trip you could go out with out the trlr and rent a uhaul or something to come back with. You would only be hauling the trlr one way then.