You're the only one that can truly answer that question, although I personally never wanted any reminders of my driving misadventures. They got fixed as soon as I could afford it.

 

I had a friend with a 1914 T that had a dent where Robert Redford had backed into a rear fender. He kept the dent and drove the car for years with the dent.
As others have said, it depends on your intentions for the truck.

 

my lady has a 51 caddy that was her 1st car. she had it painted when she 1st got it, and other than wash and wax, never did another thing to it. 15 years ago, I wanted to refresh it, but she said no, she wanted it like she had it. now the car is so rusted, it can't be saved. sometimes memories need to be keept in pictures, if you want to save the item. just my .02

 

I haven't seen any trucks for sale at Barrett-Jackson with a dent and a placard explaining the dent's origin. However, you can never underestimate the power of salesmanship. I have heard stories of Eskimos buying air conditioners. No offense to Eskimo's but the few that do may be under the broad brush labeled by P.T. Barnum.

If you do plan on selling the truck with the dent, there's a great pawn shop in Vegas that will give you top dollar; ask for Chumlee.

 

Global warming!