Good news about my incident with the tow dolly!
Well I filed a claim with U-Haul's insurance. I was told to go to my local stealership and have them write up an estimate for me. Once I get that, I need to email a copy of that, the registration and send in pictures of the damage. Once they get the estimate, they're going to cut me a check.
I'm still trying to decide on whether or not I get the dent fixed and have the tailgate repainted, or pull the dent myself and hit it with some touchup paint. I could use the money for my 4Runner.