Yes, cross country 45' gooseneck with 5 horses in it just to name an instance. Also had to learn to pull the trailer before I could get my license.
I said air bags weren't worth it because it's just not worth it on a 1/2 ton because you should just upgrade to a 3/4 ton at that point. No point in spending the money for little results.
Good trailer brakes and a good controller make a world of difference, esp if he travels light, which he said he will be.
I'm still laughing at your comment, having to pull a trailer is almost like a way of life in my family. Hell, my SISTER has probably pulled more gooseneck trailers than anyone on this site, LOL